1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Amino-4-fluorobenzamide

HRID 1424444Notes

Reaction equation

HRID 1424444 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C1C=CC2N(O)N=[N:18]C=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.N.CO>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27249674-Fluoroanthranilic acidHCID 21705897Ammonia methanol

Product 1

HCID 102410042-Amino-4-fluorobenzamideYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-amino-4-fluorobenzoic acid (4.0 g, 25.8 mmol) in degassed DMF (50 mL) were added HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.94 g, 31 mmol) and 2N NH3/MeOH (18 mL, 36.1 mmol). The solution was stirred at rt for 48 h, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 2-amino-4-fluorobenzamide as a solid (2.89 g, 66%). 1H NMR (300 MHz, DMSO-d6) δ 6.28 (m, 1H), 6.44 (m, 1H), 6.90 (br s, 2H), 7.08 (m, 1H), 7.58 (m, 1H), 7.71 (br d, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-28a63a4fa3c441b7b9f1620445c88dd4
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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