Ammonium Chloride → HCID 18992079, compound

HRID 375762Notes

Reaction equation

HRID 375762 reaction equation
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[C:9](O)[CH:10]=1)[C:5]([OH:7])=[O:6].[Cl-].[NH4+:14]>N>[NH2:14][C:9]1[CH:10]=[C:2]([OH:1])[C:3]([CH3:12])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 10953921HCID 10953921, compound

Product 1

HCID 18992079HCID 18992079, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 7.00 g of 3,5-dihydroxy-2-methylbenzoic acid, 5.40 g of ammonium chloride, and 20 ml of 25% aqueous ammonia was heated to 180° C. for 40 hours in a pressure vessel. After cooling, the mixture was evaporated in vacuo. The residue was taken up in 230 ml of 6N hydrochloric acid, and the mixture was heated at reflux for 16 hours. After cooling, unsoluble material was removed by filtration, and the filtrate was evaporated in vacuo. The residue was supended in 100 ml of water, the pH of the suspension was adjusted to 4.5 by the addition of 3N sodium hydroxide, and the mixture was cooled to 0° C. for 30 minutes. The precipitate was isolated by filtration and dried to give 2.50 g of 5-amino-3-hydroxy-2-methylbenzoic acid as white crystals, m.p. >250° C.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was evaporated in vacuo
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 16 hours
  5. temperatureAfter cooling
  6. customunsoluble material was removed by filtration
  7. customthe filtrate was evaporated in vacuo
  8. additionthe pH of the suspension was adjusted to 4.5 by the addition of 3N sodium hydroxide
  9. temperaturethe mixture was cooled to 0° C. for 30 minutes
  10. customThe precipitate was isolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-60cd4587578b4aff8af99963c7df7488
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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