Hydrochloric Acid → 2-Acetylbenzo[b]thiophene

HRID 1788857Notes

Reaction equation

HRID 1788857 reaction equation
[S:1]1[CH:5]2[CH2:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH3:10][C:11](N(C)C)=[O:12].[OH-].[K+].Cl>C(O)C.[Cu]>[C:11]([C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)(=[O:12])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 31374DimethylacetamideHCID 21584106HCID 21584106, compound

Product 1

HCID 898052-Acetylbenzo[b]thiopheneYield 70%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Procedure

The amino ester (2) was converted to the diazonium salt and reduced by boiling in ethanol containing finely divided copper to give the pure ester (3). Hydrolysis of the ester with aqueous ethanolic KOH followed by acidification with 5M HCl, gave the acid (4) in approximately 70% yield. The acid was converted to the corresponding acid chloride (5) by reaction with SOCl2.

Sources & evidence

ORD record
ord-68c35c50649b4a169b7dad29368e7ca8
Source dataset
uspto-grants-1987_08
Patent number
US04685783

Reaction notes

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