Methylamine → HCID 10058985, compound

HRID 1608235Notes

Reaction equation

HRID 1608235 reaction equation
C([NH:4][C:5]1[CH:13]=[C:12](Cl)[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C.[CH3:18][NH2:19]>>[NH2:4][C:5]1[CH:13]=[C:12]([NH:19][CH3:18])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 10083877HCID 10083877, compound

Product 1

HCID 10058985HCID 10058985, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 2-acetylamino-4-chloro-5-nitrobenzoic acid (10.0 g) and 40% aqueous methylamine solution (60 ml) is stirred at 80° C. for 10 hours and then evaporated under reduced pressure. To the residue is added 40% aqueous methylamine solution (100 ml), and the resulting solution is stirred at 80° C. for 20 hours. After cooling, the mixture is diluted with water (50 ml) and then adjusted to the pH of about 4 with acetic acid. The precipitate is collected and recrystallized from acetonitrile to give the title compound (7.6 g), mp 260°-272° C.

Workup

  1. customevaporated under reduced pressure
  2. additionTo the residue is added 40% aqueous methylamine solution (100 ml)
  3. stirringthe resulting solution is stirred at 80° C. for 20 hours
  4. temperatureAfter cooling
  5. additionthe mixture is diluted with water (50 ml)
  6. customThe precipitate is collected
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-538bcb7225ff4166825a3506b58ed425
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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