Hydrochloric Acid → 4-(1-Methylethoxy)-beta-oxobenzenepropanenitrile

HRID 1695234Notes

Reaction equation

HRID 1695234 reaction equation
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[H-].[Na+].[CH3:17][C:18]#[N:19].Cl>C1(C)C=CC=CC=1>[CH:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3](=[O:14])[CH2:17][C:18]#[N:19])=[CH:9][CH:8]=1)([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 3015807Methyl 4-(1-methylethoxy)benzoate

Product 1

HCID 203875144-(1-Methylethoxy)-beta-oxobenzenepropanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-Isopropoxy-benzoic acid methyl ester (2.2 g, 11.2 mmol, 1.0 eq) in dry toluene (15 mL) under N2, NaH (50-60% dispersion in mineral oil, 1.1 g, 22.4 mmol, 2.0 eq) was added. The mixture was heated at 80° C. and then dry CH3CN was added dropwise (2.8 mL, 56.0 mmol, 5.0 eq). The reaction was heated for 18 hours, then was allowed to cool down to room temperature and acidified with HCl 2N. The organic phase was recovered and 2.0 g of crude were obtained and it was used for cyclization without further purification.

Workup

  1. temperatureThe reaction was heated for 18 hours
  2. temperatureto cool down to room temperature
  3. customThe organic phase was recovered
  4. custom2.0 g of crude were obtained
  5. customit was used for cyclization without further purification

Sources & evidence

ORD record
ord-009cc470c01b4f7bba83b356848fb8bf
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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