HCID 20359373, compound → 3-(2-Dimethylaminoethyl)-3,4-dihydro-3-phenylisocoumarin

HRID 2083169Notes

Reaction equation

HRID 2083169 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][C:5]([OH:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9](NC)=[O:10]>ClC1C=CC=CC=1Cl>[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][C:5]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6][C:7]2[C:8](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:9](=[O:10])[O:23]1

Participants

3

Reactant 1

HCID 20359373HCID 20359373, compound

Product 1

HCID 101085553-(2-Dimethylaminoethyl)-3,4-dihydro-3-phenylisocoumarin

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a flask equipped with a stirrer, condenser and gas inlet tube maintained under a nitrogen atmosphere there is added at room temperature 16.3 g (0.05 mole) of 2-(β-[2-dimethylaminoethyl]-β-hydroxyphenethyl)-N-methylbenzamide and 170 ml of o-dichloro benzene. Stirring is initiated and the mixture is heated at reflux for 18 hours. The excess o-dichlorobenzene is then removed by distillation in vacuo and the resulting oil is crystallized from ether to give 3-[2-dimethylaminoethyl]-3,4-dihydro-3-phenylisocoumarin; m.p. 95.0°-95.5° C.

Workup

  1. customTo a flask equipped with a stirrer, condenser and gas inlet tube
  2. temperaturemaintained under a nitrogen atmosphere
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 18 hours
  5. customThe excess o-dichlorobenzene is then removed by distillation in vacuo
  6. customthe resulting oil is crystallized from ether

Sources & evidence

ORD record
ord-4b8d9011e2374a94af88b6841bd6ac4d
Source dataset
uspto-grants-1978_04
Patent number
US04083997

Reaction notes

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