Benzoylacetonitrile → HCID 85446889, compound

HRID 1085158Notes

Reaction equation

HRID 1085158 reaction equation
[C:1]([CH2:9][C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[N:36]([O-])=[O:37].[Na+]>O>[OH:37][N:36]=[C:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 64799BenzoylacetonitrileHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 85446889HCID 85446889, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of benzoylacetonitrile (11.7 g, 80.7 mmol) in a mixture of glacial acetic (34 ml) and water (1 ml) was stirred vigorously at 10° C. whilst an aqueous solution of sodium nitrite (6.1 g, 88.4 mmol in 7 ml) was added dropwise over 30 minutes. The mixture was stirred for 1 hour at room temperature and then poured into iced water (600 ml). The yellow solid which precipitated was filtered off, washed with water (100 ml) and dried, giving the title compound, 7.8 g (56%). m.p. 126°-128° C. (literature m.p. 117°-119° C.; Ger. Offen. 2,722,416 (1978).

Workup

  1. additionwas added dropwise over 30 minutes
  2. customThe yellow solid which precipitated
  3. filtrationwas filtered off
  4. washwashed with water (100 ml)
  5. customdried

Sources & evidence

ORD record
ord-6072e71bb257424fbc953473da49965e
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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