Ammonia → HCID 86658536, compound

HRID 1672218Notes

Reaction equation

C[N:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[C:16]([O:20][C:21](=[O:30])[NH:22][CH:23]1[CH2:28]CC(=O)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].N>>[C:16]([O:20][C:21](=[O:30])[NH:22][CH:23]1[CH2:24][CH2:25][C:3]2[N:2]=[C:7]([CH3:8])[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[CH2:28]1)([CH3:18])([CH3:19])[CH3:17]

Participants

Reactant 3

HCID 222Ammonia

HCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamate

HCID 13412621HCID 13412621, compound

Product 1

HCID 86658536HCID 86658536, compoundYield 28.3%

Conditions

Temperature: 60 °C

Procedure

To a sealed tube was added 1,6-dimethyl-3,5-dinitropyridin-2(1H)-one (0.16 g, 0.76 mmol), tert-butyl(4-oxocyclohexyl)carbamate (0.19 g, 0.91 mmol), and ammonia (1M in methanol, 9 mL). The resulting mixture was allowed to stir for 5 h at 60° C. and then allowed to cool to rt and concentrated. The residue was purified by column chromatography to give tert-butyl(2-methyl-3-nitro-5,6,7,8-tetrahydroquinolin-6-yl)carbamate (0.066 g, 28%) as a solid.

Workup

temperatureto cool to rt
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-ce05a3bf330747b88ca56377e69b3a22
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998952B2

Reaction notes

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