Sodium Hydroxide → (2-Amino-benzo[b]thiophen-3-yl)-phenyl-methanone

HRID 133504Notes

Reaction equation

HRID 133504 reaction equation
[C:1]([C:9]1[C:10]2[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=2[S:12][C:13]=1[NH:14]C(=O)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:14][C:13]1[S:12][C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=2[C:9]=1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68896641N-(3-benzoyl-benzo[b]thiophen-2-yl)-acetamide

Product 1

HCID 68896066(2-Amino-benzo[b]thiophen-3-yl)-phenyl-methanoneYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 0.26 g (0.90 mmol) N-(3-benzoyl-benzo[b]thiophen-2-yl)-acetamide in 20 ml ethanol was added 1 ml aqueous sodium hydroxide (1 M). The mixture was heated at 85° C. for 1 hour and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 6:1) afforded 65 mg (25%) (2-amino-benzo[b]thiophen-3-yl)-phenyl-methanone as an orange solid. ES-MS m/e (%): 254 (M+H+, 100).

Workup

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a46f72de75e444209957e5b06e1642ac
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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