Water → HCID 178438844, compound

HRID 1155195Notes

Reaction equation

HRID 1155195 reaction equation
[CH:1]([C:4]1[CH:17]=[C:16]2[C:7]([O:8][C:9]3[CH:10]=[C:11]([C:20]#[N:21])[C:12](N)=[N:13][C:14]=3[C:15]2=[O:18])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].N([O-])=[O:23].[Na+].O>C(O)(=O)C>[CH:1]([C:4]1[CH:17]=[C:16]2[C:7]([O:8][C:9]3[CH:10]=[C:11]([C:20]#[N:21])[C:12]([OH:23])=[N:13][C:14]=3[C:15]2=[O:18])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 20561050HCID 20561050, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178438844HCID 178438844, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.5 g of 7-isopropyl-2-amino-3-cyano-1-azaxanthone in 80 ml of acetic acid was added gradually 1.0 g of sodium nitrite at 70° C. After one hour period, 3 ml of water was added to the mixture which was heated at 70° C. for a further one hour. The solvent was distilled off under reduced pressure and then, to the residue, water was added. The yellow precipitate was collected by filtration, rinsed with water and recrystallized from ethanol to give 7-isopropyl-2-hydroxy-3-cyano-1-azaxanthone as yellow crystals, m.p.>300° C.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionto the residue, water was added
  3. filtrationThe yellow precipitate was collected by filtration
  4. washrinsed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dc5093b1bf574e54a0e8f6e427681058
Source dataset
uspto-grants-1981_11
Patent number
US04299963

Reaction notes

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