HCID 10446373, compound → HCID 10037749, compound

HRID 1708216Notes

Reaction equation

HRID 1708216 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[C:6]2[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:7]=2[S:8][C:9]=1[C:10]([NH2:12])=[O:11])[CH3:3]>C(O)(=O)C.[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][C:7]2[S:8][C:9]([C:10]([NH2:12])=[O:11])=[C:5]([O:4][CH:2]([CH3:1])[CH3:3])[C:6]=2[CH:16]=1

Participants

4

Reactant 1

HCID 10446373HCID 10446373, compound

Product 1

HCID 10037749HCID 10037749, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(1-methylethoxy) -5-nitrobenzo[b]-thiophene-2-carboxamide (104 mg, 0.37 mmol) and 5% Pd on carbon (10 mg) in 20 mL of acetic acid is hydrogenated for 1.5 hours. The catalyst is removed by filtration and the filtrate concentrated in vacuo. The crude product is chromatograhed, eluting with 1:2 hexane:ethyl acetate, providing 62 mg of 5-amino-3-(1-methylethoxy)benzo[b]thiophene-2-carboxamide (67%); mp 150°-151° C.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. washeluting with 1:2 hexane

Sources & evidence

ORD record
ord-c63ca2f0012f43f9a11ad8c899cea6d9
Source dataset
uspto-grants-1994_10
Patent number
US05356926

Reaction notes

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