Nitric Acid → 4-Hydroxy-7-(4-nitro-phenoxy)-isoquinoline-3-carboxylic acid butyl ester

HRID 250480Notes

Reaction equation

HRID 250480 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[N+:26]([O-])([OH:28])=[O:27]>C(O)(C(F)(F)F)=O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 667129514-Hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667130834-Hydroxy-7-(4-nitro-phenoxy)-isoquinoline-3-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2.0 g of 4-Hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester, Example D-7 f, was dissolved in 15 ml of TFA. 0.375 ml of fuming nitric acid was added slowly to the solution, and the resultant mixture was stirred at room temperature for 7 hours. The reaction mixture was concentrated under vacuum, and the resultant residue was purified by column chromatography on silica gel, eluting with 0-20% ethyl acetate in dichloromethane. The crude product obtained was triturated with methanol to produce 1.0 g of white solid; MS (+): m/z 383.01 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe resultant residue was purified by column chromatography on silica gel
  3. washeluting with 0-20% ethyl acetate in dichloromethane
  4. customThe crude product obtained
  5. customwas triturated with methanol

Sources & evidence

ORD record
ord-e501915b2bec45a4b0a2274aa4326b4d
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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