Acetic Anhydride → 2-Chloro-6-formylaminomethylnicotinic acid methyl ester

HRID 2076171Notes

Reaction equation

HRID 2076171 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[N:6][C:5]=1[Cl:12].[C:14](OC(=O)C)(=[O:16])C>C(O)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:14]=[O:16])=[N:6][C:5]=1[Cl:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 583245366-Aminomethyl-2-chloro-nicotinic acid methyl ester

Product 1

HCID 583245442-Chloro-6-formylaminomethylnicotinic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 6-aminomethyl-2-chloro-nicotinic acid methyl ester (740 mg, 3.7 mmol) in formic acid (18.5 mL) was added acetic anhydride (3.7 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated in vacuo and azeotroped three times with toluene to afford the title compound as a yellow oil (757 mg, 90%) which was used without purification in the next step. LCMS (method B): RT=2.20 min, [M+H]+=229.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped three times with toluene

Sources & evidence

ORD record
ord-b394e6d2ec6b4400b88c72a33e44de65
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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