Tributylamine → N-[-3-(4-chlorophenylsulfanyl)-2-methyl-4,5,6,7-tetrahydro-1H-indol-4-ylidene]hydroxylamine

HRID 1516991Notes

Reaction equation

C(N(CCCC)CCCC)CCC.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[C:30]3[C:29](=O)[CH2:28][CH2:27][CH2:26][C:25]=3[NH:24][C:23]=2[CH3:32])=[CH:17][CH:16]=1.Cl.[NH2:34][OH:35]>C(O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[C:30]3[C:29](=[N:34][OH:35])[CH2:28][CH2:27][CH2:26][C:25]=3[NH:24][C:23]=2[CH3:32])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Tributylamine (6.6 mL 28 mmol) was added to a stirred suspension of 3-(4-chlorophenylsulfanyl)-2-methyl-4,5,6,7-tetrahydro-1H-indol-4-one (8.0 g, 27 mmol) and hydroxylamine hydrochloride (1.9 g, 27 mmol) in ethanol (40 mL). The mixture was heated to 65° C. and maintained at this temperature for 4 h then allowed to cool to r.t. and left overnight. Additional hydroxylamine hydrochloride (0.15 g, 2.2 mmol) and tributylamine (1.0 mL, 4.2 mmol) were added and the mixture was re-heated to 65° C. for a further 2 h. After cooling to r.t., the solid product was collected by filtration, washed with ethanol (2×10 mL) then dried in a vacuum oven at 40° C. to give the title compound as an off-white solid; 5.71 g (68%); purity: 96.3 area % by HPLC; m/z: 307/309 (MH+); 1H-NMR: 11.26 (1H, s), 10.20 (1H, s), 7.23 (2H, m), 6.92 (2H, m), 2.62-2.58 (2H, m), 2.56-2.52 (2H, m), 2.12 (3H, s), 2.83-1.76 (2H, m).

Workup

temperaturemaintained at this temperature for 4 h
temperatureto cool to r.t.
temperaturethe mixture was re-heated to 65° C. for a further 2 h
temperatureAfter cooling to r.t.
filtrationthe solid product was collected by filtration
washwashed with ethanol (2×10 mL)
customthen dried in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-c0dc160b5c614cff8a105d66ada69b79
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227622B2

Reaction notes

Loading…