Cyclopropanecarbonyl chloride → 4,4-Dimethyl-7-(cyclopropylcarbonyl-amino)-8-nitro-2H,4H-isoquinoline-1,3-dione

HRID 47110Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([NH:12][C:13]([CH3:15])=[O:14])=[CH:9][CH:10]=2)[C:5](=[O:19])[NH:4][C:3]1=[O:20].[CH:22]1(C(Cl)=O)C[CH2:23]1>>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([NH:12][C:13]([CH:15]3[CH2:23][CH2:22]3)=[O:14])=[CH:9][CH:10]=2)[C:5](=[O:19])[NH:4][C:3]1=[O:20]

Participants

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride

HCID 118331714,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dione

Product 1

HCID 203849294,4-Dimethyl-7-(cyclopropylcarbonyl-amino)-8-nitro-2H,4H-isoquinoline-1,3-dione

Procedure

Prepared analogous to Example 1b from 5.8 gm of 4,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dione and 6.3 gm of cyclopropane carboxylic acid chloride (heating time: 30 hours).

Sources & evidence

ORD record: ord-4f6df2d7ae0e44b3a1857c035bfd45ad
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04176184

Reaction notes

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