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COC(=O)C1=CC(=C(C=C1)I)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | Methyl 3-amino-4-iodobenzoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 412947-54-7 |
| Database ID | 21628210 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
Methyl 3-amino-4-iodobenzoate (CAS 412947-54-7) 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 21628210
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-0520b2bd8ed64c779bb9a03c7fe693d2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7303bda2f53c4e07adfc8762cdbf7483Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0 g, 6.50 mmol) in 25 mL of absolute alcohol and 15 mL of glacial acetic acid was treated with iron powder (3.6 g, 65.0 mmol) and the mixture was heated at 80° C. After 1 hour, the reaction mixture was filtered through a pad of silica, washed with ethanol, and concentrated in vacuo. The residue was diluted with a solution of potassium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of 3-amino-4-iodobenzoic acid methyl ester as a white solid (88% yield). the reaction mixture was filtered through a pad of silica washed with ethanol concentrated in vacuo The residue was diluted with a solution of potassium carbonate extracted with ethyl acetate The combined organic layers were washed with brine dried over sodium sulfate filtered concentrated in vacuo
Source ID: ord-7d5b4f8cd506480dacb0dc38b550ddf1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred suspension of Methyl 3-amino-4-iodobenzoate (1.67 g, 6 mmol) and Methacrylic acid (568 mg, 6.6 mmol) in dichloromethane (60 mL) and DMF (60 mL) were added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (2.5 g, 6.6 mmol) and then a solution of N,N-diisopropylethylamine (1.16 g, 1560 μL, 9 mmol) in DMF (20 mL). The reaction mixture was stirred at ambient temperature for 24 h. The reaction medium was acidified by adding a 1.2 M hydrochloric acid solution and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), and concentrated to give the amide which was purified by flash chromatography (AcOEt/heptane: 5/5). extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) concentrated
Source ID: ord-e36ba10e1d384ecf932dd1f9042ce4aaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Amino-4-iodobenzoic acid (13.35 g, 50.8 mmol) was added to MeOH (150 mL) and SOCl2 (4.8 mL, 65.8 mmol, 1.3 equivalent) was added. The mixture was refluxed for 3 h and then volatiles were removed under reduced pressure. The residue was co-evaporated three times with MeOH and dried in vacuo (15.23 g). was added The mixture was refluxed for 3 h volatiles were removed under reduced pressure dried in vacuo (15.23 g)
Source ID: ord-b5a7e02008f34cf0bac20ad17989f0b4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred suspension of Methyl 3-amino-4-iodobenzoate (1.67 g, 6 mmol) and Methacrylic acid (568 mg, 6.6 mmol) in dichloromethane (60 mL) and DMF (60 mL) were added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (2.5 g, 6.6 mmol) and then a solution of N,N-diisopropylethylamine (1.16 g, 1560 pt, 9 mmol) in DMF (20 mL). The reaction mixture was stirred at ambient temperature for 24 h. The reaction medium was acidified by adding a 1.2 M hydrochloric acid solution and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), and concentrated to give the amide which was purified by flash chromatography (AcOEt/heptane: 5/5). extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) concentrated
Source ID: ord-3c65323397064e7ba7f03129f1b038b2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred suspension of Methyl 3-amino-4-iodobenzoate (1.67 g, 6 mmol) and Methacrylic acid (568 mg, 6.6 mmol) in dichloromethane (60 mL) and DMF (60 mL) were added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (2.5 g, 6.6 mmol) and then a solution of N,N-diisopropylethylamine (1.16 g, 1560 pt, 9 mmol) in DMF (20 mL). The reaction mixture was stirred at ambient temperature for 24 h. The reaction medium was acidified by adding a 1.2 M hydrochloric acid solution and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), and concentrated to give the amide which was purified by flash chromatography (AcOEt/heptane: 5/5). extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) concentrated
Source ID: ord-3c65323397064e7ba7f03129f1b038b2Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0 g, 6.50 mmol) in 25 mL of absolute alcohol and 15 mL of glacial acetic acid was treated with iron powder (3.6 g, 65.0 mmol) and the mixture was heated at 80° C. After 1 hour, the reaction mixture was filtered through a pad of silica, washed with ethanol, and concentrated in vacuo. The residue was diluted with a solution of potassium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of 3-amino-4-iodobenzoic acid methyl ester as a white solid (88% yield). the reaction mixture was filtered through a pad of silica washed with ethanol concentrated in vacuo The residue was diluted with a solution of potassium carbonate extracted with ethyl acetate The combined organic layers were washed with brine dried over sodium sulfate filtered concentrated in vacuo
Source ID: ord-7d5b4f8cd506480dacb0dc38b550ddf1Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0520b2bd8ed64c779bb9a03c7fe693d2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7303bda2f53c4e07adfc8762cdbf7483Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Amino-4-iodobenzoic acid (13.35 g, 50.8 mmol) was added to MeOH (150 mL) and SOCl2 (4.8 mL, 65.8 mmol, 1.3 equivalent) was added. The mixture was refluxed for 3 h and then volatiles were removed under reduced pressure. The residue was co-evaporated three times with MeOH and dried in vacuo (15.23 g). was added The mixture was refluxed for 3 h volatiles were removed under reduced pressure dried in vacuo (15.23 g)
Source ID: ord-42a579597b6340aeb176692b24cec39bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred suspension of Methyl 3-amino-4-iodobenzoate (1.67 g, 6 mmol) and Methacrylic acid (568 mg, 6.6 mmol) in dichloromethane (60 mL) and DMF (60 mL) were added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HAM) (2.5 g, 6.6 mmol) and then a solution of N,N-diisopropylethylamine (1.16 g, 1560 μL, 9 mmol) in DMF (20 mL). The reaction mixture was stirred at ambient temperature for 24 h. The reaction medium was acidified by adding a 1.2 M hydrochloric acid solution and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), and concentrated to give the amide which was purified by flash chromatography (AcOEt/heptane: 5/5). extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) concentrated
Source ID: ord-f22062d21e934f0d9fea91fbdb934b1fPubChem References
These sources are listed in the compound's public database record.
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