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

HRID 625785

Reaction equation

HRID 625785 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-1a734152fcc34c9aafc56644849d0576
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Linked notes

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