Methanol → 2-Amino-5-cyanobenzoic acid

HRID 2306690Notes

Reaction equation

HRID 2306690 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:9]2[C:5](=[C:6](SC)C(=O)[N:8]=2)[CH:4]=1)#[N:2].[OH-:15].[K+].C[OH:18]>O>[NH2:8][C:9]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[C:6]([OH:18])=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium Hydroxide2×HCID 22609789HCID 22609789, compound

Product 1

HCID 100578172-Amino-5-cyanobenzoic acidYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Air was bubbled through a stirred solution of 5-cyano-3-methylthio-2-oxoindole (18.0 g, 88.1 mmol) and potassium hydroxide (5.9 g, 105.2 mmol) in a 9:1 mixture of methanol:water at room temperature for 5 hours. Further potassium hydroxide (5.9 g, 105.2 mmol) was added and the air bubbling continued overnight. The methanol was removed in vacuo, and the residue was carefully acidifed with 2N aq. HCl. The resulting precipitate was collected by filtration, and triturated with ethyl acetate to give 2-amino-5-cyanobenzoic acid as a pale brown solid (4.8 g, 29.6 mmol, 34%); δH [2H6]DMSO 8.02 (1H, d), 7.55 (1H, dd), 7.50 (2H, br s), 6.86 (1H, d).

Workup

  1. customthe air bubbling
  2. customThe methanol was removed in vacuo
  3. filtrationThe resulting precipitate was collected by filtration
  4. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-b4ee9d605cf7458eb823676623b0f96a
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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