Malononitrile → ST050948

HRID 970392

Reaction equation

HRID 970392 reaction equation
C(N(CC)CC)C.O[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15].[C:16](#[N:20])[CH2:17][C:18]#[N:19]>CO>[NH2:20][C:16]1[O:15][C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 10785Cyclohexanone, 2-hydroxy-

Product 1

HCID 673083ST050948Yield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.1 4.8 ml of triethylamine are added dropwise to a solution of 11.0 g of 2-hydroxycyclohexanone and 9.6 g of malononitrile in 25 ml of methanol, and the mixture is stirred at room temperature for a further 4 hours. The crystals which deposit are separated off and washed with methanol, giving 12.8 g of 2-amino-4,5,6,7-tetrahydrobenzofuran-3-carbonitrile (“BA”), m.p. 179°.

Workup

  1. customThe crystals which deposit are separated off
  2. washwashed with methanol

Sources & evidence

ORD record
ord-4a7c5bb2c2bb4edc850a4550919d89b8
Source dataset
uspto-grants-2007_12
Patent number
US07312224B2

Linked notes

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