Methyl chloroformate → HCID 57733274, compound

HRID 1920758Notes

Reaction equation

[C:1]1([N:7](C2C=CC=CC=2)[NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[N:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[CH3:28])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:36]([O:38][CH3:39])=[O:37]>ClCCCl>[CH3:39][O:38][C:36]([N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:12]=1[CH3:28])=[O:10])=[O:37]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-methyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid N′-phenyl-hydrazide (5a, 490 mg, 1.3 mmol) and methyl chloroformate (0.6 ml, 8 mmol) in 1,2-dichloroethane (10 ml) was heated under microwave irradiation for 10 min at 100° C. Volatiles were removed in vacuo and the product was purified by flash chromatography (SiO2, gradient heptane-1:1 ethyl acetate/heptane) to give 190 mg of solid. LC-MS (m/z) 428.8 (MH+); tR=1.22.

Workup

customVolatiles were removed in vacuo
customthe product was purified by flash chromatography (SiO2, gradient heptane-1:1 ethyl acetate/heptane)

Sources & evidence

ORD record: ord-8b0fac9bab3748db9219da17be7f5393
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173639B2

Reaction notes

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