Ammonium Chloride → 2-Amino-3-nitrobenzamide

HRID 1469748Notes

Reaction equation

HRID 1469748 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.[N:21]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH4+].[Cl-].CCN(C(C)C)C(C)C>CS(C)=O>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:21])=[O:5]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 107974762-Amino-3-nitrobenzamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-amino-3-nitrobenzoic acid (5.00 g, 27.47 mmol) in DMSO (30 mL) were added BOP (18.21 g, 41.21 mmol), NH4Cl (4.41 g, 82.41 mmol) and DIPEA (10.63 g, 82.41 mmol) and the reaction mixture was stirred at rt for 14 h and it was quenched with ice-water and the precipitate obtained was filtered, washed with Et2O and dried to afford 4.90 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.48 (br s, 2H), 8.19-8.17 (m, 2H), 7.96-7.94 (d, J=7.2 Hz, 1H), 7.62 (br s, 1H), 6.71-6.65 (t, J=7.8 Hz, 1H).

Workup

  1. customit was quenched with ice-water
  2. customthe precipitate obtained
  3. filtrationwas filtered
  4. washwashed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-8332a041bc1c4a2cad2735023456cb06
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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