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

HRID 1881225Notes

Reaction equation

HRID 1881225 reaction equation
[Cl:1][C:2]1[C:3]2[CH:20]=[C:19]([OH:21])[C:18]([OH:22])=[CH:17][C:4]=2[S:5][C:6]=1[C:7]([N:9]1[CH2:14][CH:13]([CH3:15])[O:12][CH:11]([CH3:16])[CH2:10]1)=[O:8].[N+:23]([O-])([OH:25])=[O:24]>C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[C:3]2[CH:20]=[C:19]([OH:21])[C:18]([OH:22])=[C:17]([N+:23]([O-:25])=[O:24])[C:4]=2[S:5][C:6]=1[C:7]([N:9]1[CH2:10][CH:11]([CH3:16])[O:12][CH:13]([CH3:15])[CH2:14]1)=[O:8]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 67094324(3-Chloro-5,6-dihydroxy-benzo[b]thiophen-2-yl)-(2,6-dimethyl-morpholin-4-yl)-methanone

Product 1

HCID 15983353(3-Chloro-5,6-dihydroxy-7-nitro-benzo[b]thiophen-2-yl)-(2,6-dimethyl-morpholin-4-yl)-methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-Chloro-5,6-dihydroxy-benzo[b]thiophen-2-yl)-(2,6-dimethyl-morpholin-4-yl)-methanone (0.20 g) was dissolved in ethyl acetate and 1 N HNO3 solution in dichloromethane (0.64 ml) was added. Stirring was continued for 4 hours. 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. concentrationThe mixture was concentrated to smaller volume
  2. filtrationthe precipitate filtered
  3. washwashed with water
  4. customThe crude product was recrystallized from N,N-dimethylformamide/ethanol (25:75)

Sources & evidence

ORD record
ord-1ff14a536fa84ea5a43d51e0eb0a6a62
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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