Ammonia → 2-Amino-3-chloro-6-methylbenzamide

HRID 1841630Notes

Reaction equation

HRID 1841630 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:5]2[C:6](OC(=O)[NH:10][C:4]=12)=[O:7]>O.CN(C=O)C>[NH2:10][C:4]1[C:3]([Cl:2])=[CH:14][CH:13]=[C:12]([CH3:15])[C:5]=1[C:6]([NH2:1])=[O:7]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 57252331HCID 57252331, compound

Product 1

HCID 234468792-Amino-3-chloro-6-methylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
87.5 °C

Procedure

A solution of 59 ml (0.78 mol) of 25% strength ammonia solution in 207 ml of water and a mixture of 135.2 g (0.64 mol) of 3-chloro-6-methylisatoic anhydride in 705 ml of DMF were added simultaneously to 150 ml of water via 2 dropping funnels in the course of 30 min with stirring at 85 to 90° C., strong evolution of gas occurring. The mixture was stirred at 90° C. for 2 h and at 22° C. for 10 h. The reaction solution was concentrated in vacuo, and the residue was stirred with methyl tert-butyl ether, filtered off with suction and dried. 67.4 g (57% of theory) of the title compound were obtained as a yellowish powder of m.p. 124-128° C.

Workup

  1. stirringThe mixture was stirred at 90° C. for 2 h and at 22° C. for 10 h
  2. concentrationThe reaction solution was concentrated in vacuo
  3. stirringthe residue was stirred with methyl tert-butyl ether
  4. filtrationfiltered off with suction
  5. customdried

Sources & evidence

ORD record
ord-cc5ad54c94014e27983b732455130414
Source dataset
uspto-grants-2004_01
Patent number
US06683213B1

Reaction notes

Loading…