No renderable structure data available
CCOC(=O)C(C(=O)OCC)NC=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | diethyl 2-formamidopropanedioate |
|---|---|
| IUPAC Name | — |
| CAS Number | 6326-44-9 |
| Database ID | 80617 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
diethyl 2-formamidopropanedioate (CAS 6326-44-9) 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 80617
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-7ff412f3a8d84c17b4d1e8df39b0841eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9612d848b3ea4d2aa6094c3d91a30b8cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of (7-fluoro-1H-indol-3-ylmethyl)-dimethyl-amine (550 mg, 0.0028 mol.), 2-formylamino-malonic acid diethyl ester (640 mg, 0.0031 mol.), and NaOH (30 mg) in toluene (20 mL) under argon was refluxed for 3 days. The reaction mixture was concentrated and purified by column chromatography on silica gel using 40% ethyl acetate-hexane to give 2-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester (1.0 gm, 99%): mp 164-166° C., 1H NMR (500 MHz, CDCl3): 1.28 (t, J=7.5 Hz, 6H), 3.87 (s, 2H), 4.17-4.31 (m, 4H), 6.80 (s, 1H), 6.86-6.89 (dd, J=8.0 and 8.0 Hz, 1H), 6.97-7.01 (m, 2H), 7.27 (s, 1H), 8.18 (d, J=1.5 Hz, 1H), 8.27 (s, 1H). was refluxed for 3 days The reaction mixture was concentrated purified by column chromatography on silica gel using 40% ethyl acetate-hexane
Source ID: ord-44ebdc47458b4f898584fd9e2a46c9acConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl (formylamino)malonate (22.0 g, 0.108 mol) was added to a stirred solution of sodium ethoxide in ethanol (prepared from 2.4 g of sodium and 250 mL of ethanol, 0.10 mol). After 5 min, 8-(bromomethyl)quinoline (22.0 g, 0.10 mol) was added and the solution was stirred for an additional 15 minutes. The solvent was removed under reduced pressure and the product was partitioned between ethyl acetate and water. The ethyl acetate was removed and the residual oil was crystallized from ether to give 19.9 g (58%) of diethyl (formylamino)(8-quinolinylmethyl)propanedioate, mp 120°-122° C. Anal. Calcd. for C18H20N2O5 : C, 62.78; H, 5.85; N, 8.14. Found: C, 62.53; H, 6.03; N, 8.07. The solvent was removed under reduced pressure the product was partitioned between ethyl acetate and water The ethyl acetate was removed the residual oil was crystallized from ether
Source ID: ord-c7e9f2ae288440aba73aa4f12ce073deConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of (7-fluoro-1H-indol-3-ylmethyl)-dimethyl-amine (550 mg, 0.0028 mol.), 2-formylamino-malonic acid diethyl ester (640 mg, 0.0031 mol.), and NaOH (30 mg) in toluene (20 mL) under argon was refluxed for 3 days. The reaction mixture was concentrated and purified by column chromatography on silica gel using 40% ethyl acetate-hexane to give 2-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester (1.0 gm, 99%): mp 164-166° C., 1H NMR (500 MHz, CDCl3): 1.28 (t, J=7.5 Hz, 6H), 3.87 (s, 2H), 4.17-4.31 (m, 4H), 6.80 (s, 1H), 6.86-6.89 (dd, J=8.0 and 8.0 Hz, 1H), 6.97-7.01 (m, 2H), 7.27 (s, 1H), 8.18 (d, J=1.5 Hz, 1H), 8.27 (s, 1H). was refluxed for 3 days The reaction mixture was concentrated purified by column chromatography on silica gel using 40% ethyl acetate-hexane
Source ID: ord-b990747552a94b50a4ca2dd5596c7ae6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of (7-fluoro-1H-indol-3-ylmethyl)-dimethyl-amine (550 mg, 0.0028 mol.), 2-formylamino-malonic acid diethyl ester (640 mg, 0.0031 mol.), and NaOH (30 mg) in toluene (20 mL) under argon was refluxed for 3 days. The reaction mixture was concentrated and purified by column chromatography on silica gel using 40% ethyl acetate-hexane to give 2-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester (1.0 gm, 99%): mp 164-166° C., 1H NMR (500 MHz, CDCl3): 1.28 (t, J=7.5 Hz, 6H), 3.87 (s, 2H), 4.17-4.31 (m, 4H), 6.80 (s, 1H), 6.86-6.89 (dd, J=8.0 and 8.0 Hz, 1H), 6.97-7.01 (m, 2H), 7.27 (s, 1H), 8.18 (d, J=1.5 Hz, 1H), 8.27 (s, 1H). was refluxed for 3 days The reaction mixture was concentrated purified by column chromatography on silica gel using 40% ethyl acetate-hexane
Source ID: ord-44ebdc47458b4f898584fd9e2a46c9acConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl (formylamino)malonate (22.0 g, 0.108 mol) was added to a stirred solution of sodium ethoxide in ethanol (prepared from 2.4 g of sodium and 250 mL of ethanol, 0.10 mol). After 5 min, 8-(bromomethyl)quinoline (22.0 g, 0.10 mol) was added and the solution was stirred for an additional 15 minutes. The solvent was removed under reduced pressure and the product was partitioned between ethyl acetate and water. The ethyl acetate was removed and the residual oil was crystallized from ether to give 19.9 g (58%) of diethyl (formylamino)(8-quinolinylmethyl)propanedioate, mp 120°-122° C. Anal. Calcd. for C18H20N2O5 : C, 62.78; H, 5.85; N, 8.14. Found: C, 62.53; H, 6.03; N, 8.07. The solvent was removed under reduced pressure the product was partitioned between ethyl acetate and water The ethyl acetate was removed the residual oil was crystallized from ether
Source ID: ord-c7e9f2ae288440aba73aa4f12ce073deConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl (formylamino)malonate (22.0 g, 0.108 mol) was added to a stirred solution of sodium ethoxide in ethanol (prepared from 2.4 g of sodium and 250 mL of ethanol, 0.10 mol). After 5 min, 8-(bromomethyl)quinoline (22.0 g, 0.10 mol) was added and the solution was stirred for an additional 15 minutes. The solvent was removed under reduced pressure and the product was partitioned between ethyl acetate and water. The ethyl acetate was removed and the residual oil was crystallized from ether to give 19.9 g (58%) of diethyl (formylamino)(8-quinolinylmethyl)propanedioate, mp 120°-122° C. Anal. Calcd. for C18H20N2O5 : C, 62.78; H, 5.85; N, 8.14. Found: C, 62.53; H, 6.03; N, 8.07. The solvent was removed under reduced pressure the product was partitioned between ethyl acetate and water The ethyl acetate was removed the residual oil was crystallized from ether
Source ID: ord-c7e9f2ae288440aba73aa4f12ce073deConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7ff412f3a8d84c17b4d1e8df39b0841eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9612d848b3ea4d2aa6094c3d91a30b8cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of (7-fluoro-1H-indol-3-ylmethyl)-dimethyl-amine (550 mg, 0.0028 mol.), 2-formylamino-malonic acid diethyl ester (640 mg, 0.0031 mol.), and NaOH (30 mg) in toluene (20 mL) under argon was refluxed for 3 days. The reaction mixture was concentrated and purified by column chromatography on silica gel using 40% ethyl acetate-hexane to give 2-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester (1.0 gm, 99%): mp 164-166° C., 1H NMR (500 MHz, CDCl3): 1.28 (t, J=7.5 Hz, 6H), 3.87 (s, 2H), 4.17-4.31 (m, 4H), 6.80 (s, 1H), 6.86-6.86 (dd, J=8.0 and 8.0 Hz, 1H), 6.97-7.01 (m, 2H), 7.27 (s, 1H), 8.18 (d, J=1.5 Hz, 1H), 8.27 (s, 1H). was refluxed for 3 days The reaction mixture was concentrated purified by column chromatography on silica gel using 40% ethyl acetate-hexane
Source ID: ord-83ee478bc282490a9adda1e715761b65Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl (formylamino)malonate (20.3 g, 0.1 mol) was added to a stirred solution of sodium ethoxide (250 mL of 0.4 M). 2-Nitrobenzyl chloride (17.2 g, 0.1 mol) was added, the mixture was refluxed for 2 hours and the solvent was then removed under reduced pressure. The material was partitioned between ethyl acetate and water, the ethyl acetate was separated and evaporated to give 40.3 g of crude product. The compound was crystallized from ethyl acetate:hexane to give 25.5 g of diethyl (formylamino)((2-nitrophenyl)methyl)propanedioate; mp 129°-132° C. the mixture was refluxed for 2 hours the solvent was then removed under reduced pressure The material was partitioned between ethyl acetate and water the ethyl acetate was separated evaporated to give 40.3 g of crude product The compound was crystallized from ethyl acetate
Source ID: ord-11cce98a32824fc780482f4b13fc88d1PubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.