Ammonium Chloride → HCID 52947474, compound

HRID 877456Notes

Reaction equation

[O:1]=[C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][C:9]([C:15]#[N:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH3:17][Mg]Cl.[NH4+].[Cl-]>C1COCC1>[OH:1][C:2]1([CH3:17])[C:14]2[NH:13][C:12]3[C:7](=[CH:8][C:9]([C:15]#[N:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Oxo-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (0.12 g, 0.57 mmol) was dissolved in anhydrous THF (5 mL), cooled to 0° C., and methyl magnesium chloride (0.12 g, 1.71 mmol, 3M in THF) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 3 h at room temperature then cooled to 0° C., saturated NH4Cl (10 mL) was added and then extracted with EtOAc (4×25 mL). The combined organic extracts were dried over Na2SO4 concentrated under reduced pressure to give the crude material which was purified by column chromatography [EtOAc-hexane (3:7) as eluant] to obtain the title compound (0.03 g, 23%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.4 (s, 1H), 7.9 (s, 1H), 7.42 (d, J=12.0 Hz, 1H), 7.39 (d, J=12.0 Hz, 1H), 5.0 (s, 1H), 2.64-2.61 (m, 2H), 2.0-1.7 (m, 4H), 1.4 (s, 3H). IR cm−1 2216 (CN).

Workup

temperatureThe reaction mixture was warmed to room temperature
temperaturethen cooled to 0° C.
extractionextracted with EtOAc (4×25 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure
customto give the crude material which
customwas purified by column chromatography [EtOAc-hexane (3:7) as eluant]

Sources & evidence

ORD record: ord-e3a8945ccf9842c395d2a3bcaff6dc0f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

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