HCID 178498493, compound → HCID 178524584, compound

HRID 328713Notes

Reaction equation

HRID 328713 reaction equation
[OH:1][C:2]1[C:11]2[C:10]3[C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[S:14][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]=[C:4]([C:19]([O:21]C)=[O:20])[CH:3]=1>CN(C)C=O.Cl>[OH:1][C:2]1[C:11]2[C:10]3[C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[S:14][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1

Participants

4

Reactant 1

HCID 178498493HCID 178498493, compound

Product 1

HCID 178524584HCID 178524584, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g. (0.0065 mole) of methyl 1-hydroxy[1]benzothieno[3,2-f]quinoline-3-carboxylate (about 90 percent pure) in N,N-dimethyl formamide is heated to its reflux temperature, and several drops of 10 percent aqueous hydrochloric acid are added every fifteen minutes for 2 hours. The resulting yellow solid is separated by filtration to provide 1-hydroxy[1]benzothieno[3,2-f]quinoline-3-carboxylic acid, m.p. >285° C. (dec.). Analysis: Calculated for C16H9NO3S: %C, 65.1; %H, 3.1; %N, 4.7; Found: %C, 64.9; %H, 2.9; %N, 4.8. Purity is greater than 98 percent according to nuclear magnetic resonance spectral analysis.

Workup

  1. additionA mixture of 2.0 g
  2. additionare added every fifteen minutes for 2 hours
  3. customThe resulting yellow solid is separated by filtration

Sources & evidence

ORD record
ord-619a56dacbdd42e7bb727c3fde1b3b46
Source dataset
uspto-grants-1977_04
Patent number
US04018780

Reaction notes

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