Anthranilic Acid → HCID 20315068, compound

HRID 2419191Notes

Reaction equation

HRID 2419191 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 the 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-e49d83d5676340e79182730c0c4f27ae
Source dataset
uspto-grants-1978_08
Patent number
US04105653

Reaction notes

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