Hydrochloric Acid → 2-Chloronaphthalene-1-carbonitrile

HRID 1087355Notes

Reaction equation

HRID 1087355 reaction equation
C(N[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]#[N:21])(=O)C1C=CC=CC=1.[ClH:22]>C(#N)C.[Cu](Cl)Cl>[Cl:22][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]#[N:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12758535N-(1-Cyanonaphthalen-2-yl)benzamide

Product 1

HCID 137370272-Chloronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

33.6 g (0.2 mole) of 2-aminonaphthalene-1-carbonitrile (cf. Example 1) in 250 ml of absolute acetonitrile were added at 65° C. to a suspension of 32.3 g (0.24 mole) of copper(II) chloride (anhydrous) and 30.9 g (0.3 mole) of tert-butylnitrile in 800 ml of absolute acetonitrile. After the end of gas evolution, 2,000 ml of 20% strength hydrochloric acid were added to the cooled reaction mixture, and the precipitate was isolated, washed and dried. 31.7 g (70% of theory) of the title compound of melting point 82°-83° C. (active ingredient example 1001) were obtained in this manner.

Workup

  1. customthe precipitate was isolated
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-a579d0a9f18c40e3b2b31f26e902159f
Source dataset
uspto-grants-1991_07
Patent number
US05035736

Reaction notes

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