Ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate → Ethyl 2-(aminocarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate

HRID 1680204Notes

Reaction equation

[CH:1]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[O-:19][C:20]#[N:21].[Na+]>O>[NH2:21][C:20]([N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:1]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19]

Participants

Conditions

Temperature: 10 °C

Procedure

56.2 g (0.2 mol) of ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate are heated to about 60° C. in 1,000 ml of water. A solution of 15.2 g (0.234 mol) of pulverulent sodium cyanate in 200 ml of water is added all at once. The mixture is stirred for 15 minutes and then cooled to about 10° C. The aqueous reaction phase is decanted and the compound is washed with water and recrystallised from ethanol.

Workup

customThe aqueous reaction phase is decanted
washthe compound is washed with water
customrecrystallised from ethanol

Sources & evidence

ORD record: ord-fa2cb359b0de44428aa3a55b7a0fde5a
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04272539

Reaction notes

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