2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo- → HCID 53757572, compound

HRID 1380317Notes

Reaction equation

[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:12].[Cl-].[Al+3].[Cl-].[Cl-].[C:17]1(=[O:31])[N:21]([CH2:22][C:23](Cl)=[O:24])[C:20](=[O:26])[C:19]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:18]12>ClCCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:23](=[O:24])[CH2:22][N:21]3[C:20](=[O:26])[C:19]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:18]4[C:17]3=[O:31])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:12]

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin (17.7 g) and aluminum chloride (44.5 g) in 1,2-dichloroethane (26 ml) was added dropwise a solution of 2-phthalimidoacetyl chloride (25 g) in 1,2-dichloroethane (45 ml). The reaction mixture was stirred for 6 hours at 85° C. and then 22 hours at 60° C. After cooling, the mixture was poured into ice water and extracted with chloroform. The extract was washed successively with water, an aqueous solution of sodium bicarbonate and water, dried and evaporated. The residue was triturated with ethyl acetate and the resultant precipitates were collected by filtration, washed with ethyl acetate and dried to give 18.51 g of 1-methyl-2-oxo-6-phthalimidoacetyl-1,2,3,4-tetrahydroquinoline.

Workup

custom22 hours
customat 60° C
temperatureAfter cooling
extractionextracted with chloroform
washThe extract was washed successively with water
dry with materialan aqueous solution of sodium bicarbonate and water, dried
customevaporated
customThe residue was triturated with ethyl acetate
customthe resultant precipitates
filtrationwere collected by filtration
washwashed with ethyl acetate
customdried

Sources & evidence

ORD record: ord-7d4c964e2f43453481a76204aea6cce7
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581356

Reaction notes

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