Nitric Acid → 3-Chloro-5,6-dihydroxy-7-nitro-1-benzothiophene-2-carboxylic acid

HRID 1881161Notes

Reaction equation

HRID 1881161 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]([OH:14])[C:11]([OH:15])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([OH:9])=[O:8].[N+:16]([O-])([OH:18])=[O:17]>C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]([OH:14])[C:11]([OH:15])=[C:10]([N+:16]([O-:18])=[O:17])[C:4]=2[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 13575863478400-03-2

Product 1

HCID 159829713-Chloro-5,6-dihydroxy-7-nitro-1-benzothiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Chloro-5,6-dihydroxy-benzo[b]thiophene-2-carboxylic acid was dissolved in ethyl acetate and a solution of nitric acid in dichloromethane (2M, 0.38 ml) was gradually added at 20° C. The solution was stirred 10 min at room temperature and then it was poured into ice-cold water and extracted with ethyl acetate. The organic extracts were combined, dried and evaporated to dryness. The residue was recrystallized from acetic acid.

Workup

  1. additionit was poured into ice-cold water
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was recrystallized from acetic acid

Sources & evidence

ORD record
ord-39ee5300668549faa3c61461776962b2
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

Loading…