Hydrochloric Acid → HCID 10443643, compound

HRID 1608234Notes

Reaction equation

HRID 1608234 reaction equation
C([NH:4][C:5]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([N+:17]([O-:19])=[O:18])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C.Cl.O.[OH-].[Na+]>C(O)(=O)C>[NH2:4][C:5]1[CH:13]=[C:12]([N:14]([CH3:15])[CH3:16])[C:11]([N+:17]([O-:19])=[O:18])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 10355604HCID 10355604, compound

Product 1

HCID 10443643HCID 10443643, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-acetylamino-4-dimethylamino-5-nitrobenzoic acid (6.5 g), concentrated hydrochloric acid (20 ml), and water (80 ml) is stirred at 100° C. for 30 minutes. After cooling, solid sodium hydroxide (5 g) and then 10% aqueous sodium hydroxide solution are added until the mixture becomes a clear solution. The resulting solution is adjusted to the pH of about 4 with acetic acid. The precipitate is collected and recrystallized from methanol to give the title compound (4.8 g), mp 240°-250° C.

Workup

  1. temperatureAfter cooling
  2. customThe precipitate is collected
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5e85f236bfb54e2fa3196ca248b30fe8
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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