Nitric Acid → (3-Chloro-5,6-dihydroxy-7-nitro-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone

HRID 1881228Notes

Reaction equation

HRID 1881228 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:7]2[CH:23]=[C:22]([OH:24])[C:21]([OH:25])=[CH:20][C:8]=2[S:9][C:10]=1[C:11]([N:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1)=[O:12]>ClCCl.C(OCC)(=O)C>[Cl:5][C:6]1[C:7]2[CH:23]=[C:22]([OH:24])[C:21]([OH:25])=[C:20]([N+:1]([O-:4])=[O:2])[C:8]=2[S:9][C:10]=1[C:11]([N:13]1[CH2:14][CH2:15][CH:16]([OH:19])[CH2:17][CH2:18]1)=[O:12]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 67094375(3-Chloro-5,6-dihydroxy-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone

Product 1

HCID 15983354(3-Chloro-5,6-dihydroxy-7-nitro-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1 M HNO3 in dichloromethane (0.67 ml) was added to a solution of (3-chloro-5,6-dihydroxy-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone (0.17 g) in ethyl acetate (10 ml). Stirring was continued at 60° C. for 3 hours and then at room temperature overnight. The mixture was concentrated to smaller volume and the precipitate filtered and washed with water. The crude product was recrystallized from N,N-dimethylformamide/ethanol (25:75).

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationThe mixture was concentrated to smaller volume
  4. filtrationthe precipitate filtered
  5. washwashed with water
  6. customThe crude product was recrystallized from N,N-dimethylformamide/ethanol (25:75)

Sources & evidence

ORD record
ord-affd3e60f5cb464cbf27fe0a3ce5638f
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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