Water → HCID 346836, compound

HRID 612359Notes

Reaction equation

HRID 612359 reaction equation
[OH-].[K+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])([O-:14])=O.O>CO.C(O)(=O)C>[OH:14][N:12]=[C:15]1[CH:20]=[CH:19][C:18](=[C:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:10]#[N:11])[CH:17]=[C:16]1[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 69442-NitrotolueneHCID 8794PhenylacetonitrileHCID 14797Potassium Hydroxide

Product 1

HCID 346836HCID 346836, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

39.6 g of KOH (0.6 mol, assay 85%) are dissolved in 200 ml of methanol and heated up to 55° C. To the solution are added 23.4 g (0.20 mol) of phenylacetonitrile, followed by 25 g (0.18 mol) of o-nitrotoluene. The dark red reaction mixture is stirred at 55° C. for 4 hrs. After cooling, the mixture is poured into 500 ml of water, and acidified by addition of 60 ml of acetic acid. The resulting orange precipitate is filtered, washed with water, methanol:water 1:1 (v/v), and dried under vacuum. The crude product (16.8 g, 40%) has a melting point of 161-164° C. (dec) (Lit: 161° C. dec; J. Org. Chem. 26, 4270, 1961) and is used in the next step without further purification.

Workup

  1. customThe dark red reaction mixture
  2. temperatureAfter cooling
  3. filtrationThe resulting orange precipitate is filtered
  4. washwashed with water, methanol:water 1:1 (v/v)
  5. customdried under vacuum
  6. customis used in the next step without further purification

Sources & evidence

ORD record
ord-b3de320b83bc4c56b8f6bf83cde7bd14
Source dataset
uspto-grants-1999_12
Patent number
US06004724

Reaction notes

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