4-Nitrobenzoyl chloride → 3,4-dihydro-2,2-dimethyl-6-(4-nitrobenzoyl)-4-(2-pyridyl)-2H-1-benzopyran

HRID 1073898Notes

Reaction equation

[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3]1.[Cl-].[Al+3].[Cl-].[Cl-].[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24]>[N+](C)([O-])=O>[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:34][CH:33]=3)[CH:16]=[CH:17][C:4]=2[O:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

200 mg of 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran were dissolved in 10 ml of nitromethane and the solution was cooled to 0° C. under a nitrogen atmosphere. 240 mg of finely powdered aluminum chloride were added and, after stirring at 0° C. for 5 minutes, 388 mg of 4-nitrobenzoyl chloride were added. After 16 hours at room temperature 120 mg of aluminum chloride were added and the mixture was stirred at 100° C. for 45 minutes. After dilution with diethyl ether and washing with sodium hydroxide solution the organic phase was dried over sodium sulphate and evaporated. The residue crystallized and was triturated with diethyl ether to give 150 mg of 3,4-dihydro- 2,2-dimethyl-6-(4-nitrobenzoyl)-4-(2-pyridyl)-2H-1-benzopyran.

Workup

stirringthe mixture was stirred at 100° C. for 45 minutes
washAfter dilution with diethyl ether and washing with sodium hydroxide solution the organic phase
dry with materialwas dried over sodium sulphate
customevaporated
customThe residue crystallized
customwas triturated with diethyl ether

Sources & evidence

ORD record: ord-38ab85254c3441b4b38ec8960ff80c54
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971982

Reaction notes

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