Sodium Hydroxide → 4-Acetylamino-5-chlorosalicylic acid

HRID 1606903Notes

Reaction equation

HRID 1606903 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[C:10]([Cl:17])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[C:14]([NH:13][C:11]1[CH:12]=[C:3]([OH:2])[C:4](=[CH:9][C:10]=1[Cl:17])[C:5]([OH:7])=[O:6])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 77721Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Product 1

HCID 151360454-Acetylamino-5-chlorosalicylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 16 g of methyl 2-methoxy-4-acetylamino-5-chlorobenzoate in 130 ml of methylene chloride is slowly added 100 ml of a methylene chloride solution of borontribromide (250 g BBr3 per liter) and stirring continued for 24 hours. 1N sodium hydroxide solution is then added until all material is dissolved. The two layers are separated and the aqueous layer is acidified with 1N hydrochloric acid, filtered, washed with water and evaporated to dryness to give 4-acetylamino-5-chlorosalicylic acid which is used directly in the next step.

Workup

  1. dissolutionis dissolved
  2. customThe two layers are separated
  3. filtrationfiltered
  4. washwashed with water
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-0f3288a917ab492b92ae48f51fb1ff0b
Source dataset
uspto-grants-1989_09
Patent number
US04863921

Reaction notes

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