2-Amino-5-chlorobenzoic acid → 2-amino-5-chloro-N-methoxy-N-methylbenzamide

HRID 1745855Notes

Reaction equation

HRID 1745855 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]

Participants

7

Reactant 4

HCID 124762-Amino-5-chlorobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-amino-5-chlorobenzoic acid (5.0 g, 29.1 mmol), N,O-dimethylhydroxylamine hydrochloride (3.1 g, 32.0 mmol), and HOBt (3.9 g, 29.1 mmol) in CH2Cl2 (100 mL) was cooled to 0° C. and treated with EDCI (17.3 g, 87.3 mmol). The reaction was stirred at 25° C. for 12 h, diluted with H2O, and extracted with EtOAc. The organics were dried (Na2SO4), filtered, and concentrated. Chromatography (SiO2, 1:1 Hex/EtOAc) gave 8 (3.7 g, 60%) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-97bec5ec9f1340ea9cc805b83e81ad9b
Source dataset
uspto-grants-2006_03
Patent number
US07019141B2

Reaction notes

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