Hydrochloric Acid → 3-Chloro-5,6-dihydroxy-4-nitro-1-benzothiophene-2-carboxylic acid

HRID 1881166Notes

Reaction equation

HRID 1881166 reaction equation
[Cl:1][C:2]1[C:3]2[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([OH:17])[C:11]([O:18]C)=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([OH:9])=[O:8].N1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([OH:17])[C:11]([OH:18])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 67094293HCID 67094293, compound

Product 1

HCID 159829733-Chloro-5,6-dihydroxy-4-nitro-1-benzothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To the solution of 3-chloro-5-hydroxy-6-methoxy-4-nitro-benzo[b]thiophene-2-carboxylic acid (0.2 g), pyridine (6.3 ml) in ethyl acetate (5 ml) was gradually added aluminum trichloride (0.32 g). The reaction mixture was refluxed at 90° C. for two hours. To the warm reaction (60° C.) solution was added the mixture of concentrated hydrochloric acid and ice (1:1). The product was extracted into ethyl acetate, dried and evaporated. The residue was treated with diethyl ether and the resultant solid was filtered.

Workup

  1. customTo the warm reaction (60° C.) solution
  2. additionwas added
  3. extractionThe product was extracted into ethyl acetate
  4. customdried
  5. customevaporated
  6. additionThe residue was treated with diethyl ether
  7. filtrationthe resultant solid was filtered

Sources & evidence

ORD record
ord-91a69963a6c242b99ec8ae80238e5c42
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

Loading…