1-Hydroxybenzotriazole → 2-Amino-3-methylbenzamide

HRID 1424440Notes

Reaction equation

HRID 1424440 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][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.N.CO>CN(C=O)C>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 781012-Amino-3-methylbenzoic acidHCID 81531DiisopropylethylamineHCID 21705897Ammonia methanol

Product 1

HCID 142218072-Amino-3-methylbenzamideYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-amino-3-methylbenzoic acid (4.0 g, 26.5 mmol) in degassed DMF (40 mL) were added HOBt (4.28 g, 31.7 mmol), DIEA (5.52 mL, 31.7 mmol), and 2N NH3/MeOH (19 mL, 37.1 mmol). The solution was stirred at rt for 16 h, then. the mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-60% EtOAc/hexanes to afford 2-amino-3-methylbenzamide as a solid (2.52 g, 63%). 1H NMR (300 MHz, DMSO-d6) δ 2.07 (s, 3H), 6.40-6.47 (m, 3H), 7.06 (m, 2H), 7.42 (d, 1H), 7.72 (br d, 1H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 10-60% EtOAc/hexanes

Sources & evidence

ORD record
ord-5c5af9da58ab43919e0b71e5f9b07164
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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