Potassium Hydroxide → Thiopyrano[3,4-b]indole-1-acetic acid, 1,3,4,9-tetrahydro-1-methyl-

HRID 1833696Notes

Reaction equation

C[O:2][C:3](=[O:19])[CH2:4][C:5]1([CH3:18])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][S:6]1)=[CH:16][CH:15]=[CH:14][CH:13]=3.[OH-].[K+]>>[CH3:18][C:5]1([CH2:4][C:3]([OH:19])=[O:2])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][S:6]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 538355841-Methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid methyl ester

Product 1

HCID 12255469Thiopyrano[3,4-b]indole-1-acetic acid, 1,3,4,9-tetrahydro-1-methyl-

Procedure

This ester is then treated with aqueous alcoholic KOH in the manner described for the esters in Examples 1 and 2 to afford the title compound, m.p. 147° - 149° C., nmr (CDCl3) δ1.86 (S, 3H), 3.06, 8.12 (6H), 7.35 (multiplet, 4H), 8.71 (1H), 10.31 (1H), after recrystallization from benzene-hexane.

Sources & evidence

ORD record: ord-0b68377c683b4349b96a5c34060fb474
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04066780

Reaction notes

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