Ammonia → HCID 86658536, compound

HRID 2388009Notes

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.O=C1C[CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]1.N>>[CH3:8][C:7]1[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]2[CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[CH2:19][CH2:18][C:3]=2[N:2]=1

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-710cd04e6c38418dbe2ec5f2eed59f78
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268992B2

Reaction notes

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