Anthranilic Acid → HCID 20315068, compound

HRID 1287953Notes

Reaction equation

HRID 1287953 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)N.[ClH:11].N([O-])=O.[Na+].[C:16](#[N:19])[CH:17]=[CH2:18]>[Cl-].[Na+].O.CC(C)=O.C(O)(=O)C>[Cl:11][CH:17]([C:16]#[N:19])[CH2:18][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9]

Participants

8

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric Acid2×HCID 7855AcrylonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 20315068HCID 20315068, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

274 parts of anthranilic acid are mixed with 650 parts of hydrochloric acid (density 1.15) and 560 parts of crystallizable acetic acid. The mixture is cooled externally to 0° C. by means of a brine, then diazotised by means of 138 parts of sodium nitrite. The solution of the diazo derivative is then poured, whilst being stirred, into a mixture of 190 parts of acetone and 370 parts of acrylonitrile, at the same time as a solution of 6 parts of cuprous chloride in 50 parts of hydrochloric acid (density 1.08). The reaction is exothermic. After the diazonium chloride has disappeared and after decantation and crystallization in water, 330 parts of a product are obtained which has a melting point of 116°-117° C. and which is recrystallized in xylene. 314 parts of 2-(2-chloro-2-cyanoethyl) benzoic acid are obtained. M.P.: 119°-120° C.

Workup

  1. customafter decantation and crystallization in water
  2. custom330 parts of a product are obtained which
  3. customis recrystallized in xylene

Sources & evidence

ORD record
ord-9c35e1e7a2fa45079fad4a576af1933b
Source dataset
uspto-grants-1976_10
Patent number
US03987027

Reaction notes

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