Acetic Acid → HCID 22337641, compound

HRID 887327Notes

Reaction equation

HRID 887327 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([OH:14])[N:8]=[CH:9]2)([O-:3])=[O:2].[C:15](O)(=[O:17])[CH3:16].N1C=CC=CC=1>C(OC(=O)C)(=O)C>[C:15]([O:14][C:7]1[N:8]=[CH:9][C:10]2[C:5]([CH:6]=1)=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=[CH:12][CH:11]=2)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1049PyridineHCID 178526523HCID 178526523, compound

Product 1

HCID 22337641HCID 22337641, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

5-Nitro-3-isoquinolinol (3.40 g, 17.9 mmol) in acetic anhydride (40 mL) was treated with acetic acid (5 mL) and pyridine (5 mL) and heated at 120° C. for 2 hours. The mixture was cooled to room temperature and concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. MS (ESI+) m/z 233 (M+H)+; MS (ESI−) m/z 231 (M−H)−; 1H NMR (DMSO, 300 MHz) isomers δ 2.39 (s, 3H), 7.88 (m, 1H), 8.27 (m, 1H), 8.50 (m, 1H), 8.65, 8.74 (d, J 7.8, 1H), 9.47, 9.55 (s, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19c4073004094b2f8caeea625ba836f7
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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