Potassium Carbonate → Benzo[b]thiophene-2-carboxylic acid, 3-amino-6-chloro-, methyl ester

HRID 235065

Reaction equation

HRID 235065 reaction equation
[N+]([C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[C:13]([O:17][CH2:18]C)(=[O:16])[CH2:14][SH:15].C(=O)([O-])[O-].[K+].[K+].CCCCCC.CCOC(C)=O>CCO>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:4]=2[S:15][C:14]=1[C:13]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 969244-Chloro-2-nitrobenzonitrileHCID 21226206Ethyl acetate hexane

Product 1

HCID 14916787Benzo[b]thiophene-2-carboxylic acid, 3-amino-6-chloro-, methyl esterYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-nitro-4-chlorobenzonitrile (1.94 g, 10.6 mmol) was treated with 1 eq of ethyl thioglycolate and 1 eq potassium carbonate in EtOH as described in Example 41A to give after chromatography (4:1 hexane/EtOAc) the title compound in 31% yield. 1H NMR (300 MHz, CDCl3) d 1.38 (t, J=7 Hz, 3H), 4.36 (q, J=7 Hz, 2H), 5.85 (bs, 2H), 7.33 (dd, J=9,2 Hz, 1H), 7.54 (d, J=9 Hz; 1H), 7.1 (d, J=2 Hz, 1H). MS (DCI/NH3) m/e 256 (M+H)+.

Sources & evidence

ORD record
ord-6bc4b181c0634fd8a28e20f02217f777
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Linked notes

Loading…