No renderable structure data available
C1=CC=C2C=C(C(=CC2=C1)C(=O)NN)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-hydroxynaphthalene-2-carbohydrazide |
|---|---|
| IUPAC Name | — |
| CAS Number | 5341-58-2 |
| Database ID | 72699 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-hydroxynaphthalene-2-carbohydrazide (CAS 5341-58-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 72699
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ceda7c58d6fa41b6b61759eeca32bd6aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of salicylic aldehyde and 3-hydroxy-2-naphthoic hydrazide gave a pale yellow solid (94%): mp >285° C.; 1H NMR d 11.69 (br s, 1H), 10.97 (br s, 1 H), 10.79 (s, 1 H), 8.24 (s, 1 H), 8.02 (s, 1 H), 7.45 (d, 1 H, J=8.1 Hz), 7.31 (d, 1 H, J=8.1 Hz), 7.12 (dd, 1 H, J=7.8, 0.9 Hz), 7.05 (t, 1 H, J=7.5 Hz), 6.89 (s, 1 H), 6.86 (m, 2H), 6.51 (d, 1 H, J=8.1 Hz), 6.48 (t, 1H, J=7.5 Hz); 13C NMR d 163.62, 157.54, 154.08, 148.83, 135.94, 131.64, 130.37, 129.49, 128.70, 128.33, 126.79, 125.89, 123.86, 119.99, 119.44, 118.68, 116.48, 110.63; HRMS Calcd for C18H14N2O3 :306.1004, found 306.0977; Anal. (C18H14N2O3) C, H, N.
Source ID: ord-45d83b3f77a5489f92acab6a46408a07Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of salicylic aldehyde and 3-hydroxy-2-naphthoic hydrazide gave a pale yellow solid (94%): mp >285° C.; 1H NMR d 11.69 (br s, 1H), 10.97 (br s, 1 H), 10.79 (s, 1 H), 8.24 (s, 1 H), 8.02 (s, 1 H), 7.45 (d, 1 H, J=8.1 Hz), 7.31 (d, 1 H, J=8.1 Hz), 7.12 (dd, 1 H, J=7.8, 0.9 Hz), 7.05 (t, 1 H, J=7.5 Hz), 6.89 (s, 1 H), 6.86 (m, 2H), 6.51 (d, 1 H, J=8.1 Hz), 6.48 (t, 1H, J=7.5 Hz); 13C NMR d 163.62, 157.54, 154.08, 148.83, 135.94, 131.64, 130.37, 129.49, 128.70, 128.33, 126.79, 125.89, 123.86, 119.99, 119.44, 118.68, 116.48, 110.63; HRMS Calcd for C18H14N2O3 :306.1004, found 306.0977; Anal. (C18H14N2O3) C, H, N.
Source ID: ord-45d83b3f77a5489f92acab6a46408a07Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 1naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide gave a pale yellow solid (76%): mp 214° C.; 1H NMR d 11.73 (br s, 1 H), 11.05 (br s, 1 H), 8.72 (s, 1 H), 8.52 (d, 1 H, J=8.4 Hz), 8.13 (s, 1 H), 7.60-6.80 (m, 11 H); 13C NMR d 164.00, 154.31, 148.56, 135.99, 133.57, 130.80, 130.40. 130.30, 129.48, 128.81, 128.78, 128.29, 128.12, 127.37, 126.85, 126.31. 125.89, 125.54, 124.39, 123.84, 120.13, 110.75; HRMS Calcd for C22H16N2O2 :340.1212, found 340.1208; Anal. (C22H16N2O2) C, H, N.
Source ID: ord-36607ec1d42940318737e612c15177beConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 2, 6-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded a yellow solid (72%): mp>280° C.; 1H NMR d 11.89 (s, 1 H), 11.75 (br s, 1 H), 10.90 (br s, 1 H), 9.14 (s, 1 H), 9.03 (s, 1 H), 8.06 (s, 1 H), 7.75 (d, 1 H, J=9.0 Hz), 7.48 (d, 1 H, J=8.4 Hz), 7.33 (d, 1 H, J=8.4 Hz), 7.28 (d, 1 H, J=9.0 Hz), 7.07 (t, 1 H, J=7.6 Hz), 6.92 (t, 1 H, J=7.4 Hz), 6.75-6.67 (m, 3 H), 6.90 (m, 2 H); 13C NMR d 163.06, 155.90, 153.93, 153.44, 147.82, 135.94, 131.34, 130.57, 129.35, 128.69, 128.34, 126.81, 125.87, 125.66, 123.88, 122.58, 119.86, 119.68, 119.04, 110.62, 110.45, 108.82; HRMS Calcd for C22H16N2O4 :372.1110, found 372.1095; Anal. (C22H16N2O4 0.4 H2O) C, H, N.
Source ID: ord-daaf56fbd8174269a850fcbfb24aacbcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 2, 6-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded a yellow solid (72%): mp>280° C.; 1H NMR d 11.89 (s, 1 H), 11.75 (br s, 1 H), 10.90 (br s, 1 H), 9.14 (s, 1 H), 9.03 (s, 1 H), 8.06 (s, 1 H), 7.75 (d, 1 H, J=9.0 Hz), 7.48 (d, 1 H, J=8.4 Hz), 7.33 (d, 1 H, J=8.4 Hz), 7.28 (d, 1 H, J=9.0 Hz), 7.07 (t, 1 H, J=7.6 Hz), 6.92 (t, 1 H, J=7.4 Hz), 6.75-6.67 (m, 3 H), 6.90 (m, 2 H); 13C NMR d 163.06, 155.90, 153.93, 153.44, 147.82, 135.94, 131.34, 130.57, 129.35, 128.69, 128.34, 126.81, 125.87, 125.66, 123.88, 122.58, 119.86, 119.68, 119.04, 110.62, 110.45, 108.82; HRMS Calcd for C22H16N2O4 :372.1110, found 372.1095; Anal. (C22H16N2O4 0.4 H2O) C, H, N.
Source ID: ord-daaf56fbd8174269a850fcbfb24aacbcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 2, 7-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded yellow crystals (83%) [recrystallized from DMSO/H2O (8:2, v/v)]: mp225° C. (dec); 1H NMR d 12.75 (s, 1 H), 12.24 (s, 1 H), 11.27 (s, 1 H), 9.93 (s, 1 H), 9.40 (s, 1H), 8.50 (s, 1 H), 7.95 (d, 1 H, J=8.1 Hz), 7.80 (d, 2 H, J=8.7 Hz), 7.73 (d, 1 H, J=8.7 Hz), 7.54 (t, 1 H, J=7.5 Hz), 7.39 (t, 1 H, J=7.5 Hz), 7.37 (s, 1 H), 6.98 (d, 2 H, J=8.7 Hz); HRMS Calcd for C22H16N2O4 :372.1110, found 372.1099; Anal. (C22H16N2O4 1.4 DMSO) C, H, N. recrystallized from DMSO/H2O (8:2
Source ID: ord-2ac4037a3e134186bbceba22869de581Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 2, 4-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded a yellow crystal (83%) [recrystallized from DMSO/H2O (8:2, v/v)]: mp>280° C. (dec); 1H NMR d 12.42 (br s, 1 H), 11.65 (s, 1 H), 10.96 (br s, 1 H), 10.59 (s, 1 H), 8.99 (s, 1H), 8.07 (s, 1H), 7.77 (d, 1 H, J=8.4 Hz), 7.67 (d, 1 H, J=8.4 Hz), 7.48 (d, 1 H, J=8.1 Hz), 7.32 (d, 1H, J=8.4 Hz), 7.13 (t, 1H, J=7.5 Hz), 7.06 (t, 1 H, J=7.5 Hz), 6.91 (s, 1 H), 6.90 (m, 2 H); 13C NMR d 162.92, 160.47. 157.70, 154.20, 148.22, 135.97, 132.99, 130.33, 128.72, 128.33 (2 C), 126.84, 125.92, 123.91, 122.94, 122.55, 120.80, 120.32, 119.66, 110.70, 101.38, 100.49; HRMS Calcd for C22H16N2O4 :372.1110, found 372.1095; Anal. (C22H16N2O4 2DMSO H2O) C, H, N.
Source ID: ord-f3b1c4bf0247451dbebc27292ef98ba6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 2, 4-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded a yellow crystal (83%) [recrystallized from DMSO/H2O (8:2, v/v)]: mp>280° C. (dec); 1H NMR d 12.42 (br s, 1 H), 11.65 (s, 1 H), 10.96 (br s, 1 H), 10.59 (s, 1 H), 8.99 (s, 1H), 8.07 (s, 1H), 7.77 (d, 1 H, J=8.4 Hz), 7.67 (d, 1 H, J=8.4 Hz), 7.48 (d, 1 H, J=8.1 Hz), 7.32 (d, 1H, J=8.4 Hz), 7.13 (t, 1H, J=7.5 Hz), 7.06 (t, 1 H, J=7.5 Hz), 6.91 (s, 1 H), 6.90 (m, 2 H); 13C NMR d 162.92, 160.47. 157.70, 154.20, 148.22, 135.97, 132.99, 130.33, 128.72, 128.33 (2 C), 126.84, 125.92, 123.91, 122.94, 122.55, 120.80, 120.32, 119.66, 110.70, 101.38, 100.49; HRMS Calcd for C22H16N2O4 :372.1110, found 372.1095; Anal. (C22H16N2O4 2DMSO H2O) C, H, N.
Source ID: ord-f3b1c4bf0247451dbebc27292ef98ba6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 2, 3-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded a yellow crystal (18%) [recrystallized from dioxane/H2O (1:1, v/v)]: mp>285° C.; 1H NMR d 13.16 (br s, 1 H), 12.27 (br s, 1 H), 11.30 (br s, 1 H), 9.74 (br s, 1 H), 9.57 (s, 1 H), 8.53 (s, 1 H), 8.17 (d, 1 H, J=8.2 Hz), 7.95 (d, 1 H, J=8.2 Hz), 7.79 (d, 1 H, J=8.0 Hz), 7.70 (d, 1 H, J=7.7 Hz), 7.54 (t, 1 H, J=7.4 Hz), 7.42-7.25 (m, 5 H); HRMS Calcd for C22H16N2O4 :372.1110, found 372.1103; Anal. (C22H16N2O4H2O) C, H, N.
Source ID: ord-83a5492faaa64fab88f6642b416e8aeeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of Example 1, condensation of 2-Hydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide gave a white solid (97%): mp >300° C.; 1H NMR d 12.70 (s, 1 H), 12.25 (br s, 1 H), 11.37 (br s, 1 H); 9.58 (s, 1 H), 8.52 (s, 1 H), 8.33 (d, 1 H, J=8.7 Hz), 7.94 (d, 2 H, J=8.7 Hz), 7.89 (d, 1 H, J=8.1 Hz), 7.78 (d, 1 H, J=8.4 Hz), 7.58 (t, 1 H, J=7.6 Hz), 7.52 (t, 1 H, J=7.5 Hz), 7.41 (m, 2 H), 7.37 (s, 1 H), 7.25 (d, 1 H, J=9.0 Hz); 13C NMR d 163.05, 158.12, 153.88, 147.57, 135.94, 132.90, 131.68, 130.62, 128.90, 128.68, 128.33, 127.79, 127.73, 126.81, 125.85, 123.86, 123.54, 120.98, 119.84, 118.87, 110.62, 108.61; HRMS Calcd for C22H16N2O3 :356.1161, found 356.1151; Anal. (C22H16N2O3) C, H, N.
Source ID: ord-fc956165d72b40b2a875c564173e60a6Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A four neck flask (1 liter) equipped with a thermometer and a stirrer was charged with 60.6 g (0.3 mol) of 3-hydroxy-2-naphthohydrazide, 36.9 g (0.45 mol) of sodium acetate and 800 ml of acetic acid and heated to 30° C. Dropwise added thereto was 50.6 g (0.36 mol) of benzoyl chloride in one hour while stirring, and stirring was continued at 30° C. for one hour. After finishing the reaction, the reaction liquid was added to 1.5 liter of deionized water and crystal was filtered off. After washing sufficiently the crystal with 1 liter of deionized water and 500 ml of methanol, it was dried under reduced pressure to obtain slightly brown crystal. A four neck flask (1 liter) equipped with a thermometer and a stirrer Dropwise added in one hour stirring the reaction the reaction liquid was filtered off After washing sufficiently the crystal with 1 liter of deionized water and 500 ml of methanol, it was dried under reduced pressure to obtain slightly brown crystal
Source ID: ord-0a0b2cc66ebc4bedbb9c1a7faad92166PubChem References
These sources are listed in the compound's public database record.
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