Sodium Hydroxide → 4-Amino-5-cyano-2-methoxybenzoic acid

HRID 345580Notes

Reaction equation

HRID 345580 reaction equation
[NH2:1][C:2]1[C:12]([C:13]#[N:14])=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[C:4]([O:15][CH3:16])[CH:3]=1.[OH-].[Na+]>O>[NH2:1][C:2]1[C:12]([C:13]#[N:14])=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15096747Ethyl 4-amino-5-cyano-2-methoxybenzoate

Product 1

HCID 150967484-Amino-5-cyano-2-methoxybenzoic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 10.69 parts of ethyl 4-amino-5-cyano-2-methoxybenzoate in 12 parts of a sodium hydroxide solution 50% and 500 parts of water was stirred and heated to 50° C. and stirring was continued for 1 hour at 50°-55° C. The reaction mixture was cooled and filtered. The filtrate was acidified with concentrated hydrochloric acid of pH 1-2. The precipitated product was filtered off, washed thoroughly with water and dried overnight at 80° C., yielding 8.6 parts (93.2%) of 4-amino-5-cyano-2-methoxybenzoic acid; mp. 236.7° C. (intermediate 111).

Workup

  1. stirringstirring
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. filtrationThe precipitated product was filtered off
  5. washwashed thoroughly with water
  6. customdried overnight at 80° C.

Sources & evidence

ORD record
ord-5ecac440754e443a8b50adbf7fdb0b38
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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