Ammonia → 4-Benzyloxy-5-methoxy-2-(4-methylbenzoyl)benzonitrile

HRID 2381242Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([O:25][CH3:26])=[CH:11][C:12](Br)=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[O:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu][C:28]#[N:29].CN1CCCC1=O.N>O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:25][CH3:26])=[CH:11][C:12]([C:28]#[N:29])=[C:13]([C:15](=[O:16])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of (5-benzyloxy-2-bromo-4-methoxyphenyl)-p-tolylmethanone (reference example 10-1) (1.11 g), copper(I)cyanide (967 mg) and 1-methyl-2-pyrrolidinone (2 mL) was irradiated with microwave to heat at 200° C. for 10 min while stirring. Water, a 28% ammonia in water and ethyl acetate were added. The separated organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with diethyl ether to give the title compound (1.08 g).

Workup

customwas irradiated with microwave
dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-8cc61f0707c54dd58ee417a99f8df97d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258162B2

Reaction notes

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