Acetic Acid → 2-[(Cyanomethyl)(phenyl)amino]-5-methoxybenzoic acid

HRID 1982415Notes

Reaction equation

HRID 1982415 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:13][O:12][C:11](=[O:21])[C:10]=2[CH:22]=1.C(O)(=O)C>O>[C:1]([CH2:13][N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:22][C:10]=1[C:11]([OH:12])=[O:21])#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 132203746-Methoxy-1-phenyl-1,2-dihydro-4H-3,1-benzoxazin-4-one

Product 1

HCID 132203752-[(Cyanomethyl)(phenyl)amino]-5-methoxybenzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 268 g (4.1 mole) of potassium cyanide in 1.6 l of water was added 1021 g (4.0 mole) of 1,2-dihydro-6-methoxy-1-phenyl-4H-3,1-benzoxazine-4-one at a rate such that the reaction mixture temperature was 35°-40° C. The resulting solution was stirred and maintained at 35°-40° C. for two hours, and then added dropwise to a solution of 8.0 l of ice water and 800 ml of acetic acid. The resulting suspended solid was filtered and washed with water to yield 1084 g (96% yield) of the crude nitrile, mp 122°-130° C. This material was used for further synthesis without additional purification.

Workup

  1. customwas 35°-40° C
  2. temperaturemaintained at 35°-40° C. for two hours
  3. filtrationwas filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-c685fb7d4dbc42ecb9f80af16fe4c2e2
Source dataset
uspto-grants-1986_06
Patent number
US04596814

Reaction notes

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