2-Aminophenol → HCID 86609052, compound

HRID 2217995Notes

Reaction equation

HRID 2217995 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].CN(C)C=O.[F:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([CH:25]=[CH:26][C:27]1[O:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=1)[N:19]=[C:18]2Cl>O>[F:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([CH:25]=[CH:26][C:27]1[O:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=1)[N:19]=[C:18]2[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8]

Participants

5

Reactant 3

HCID 58012-Aminophenol2×HCID 6228DimethylformamideHCID 72829569HCID 72829569, compound

Product 1

HCID 86609052HCID 86609052, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An Erlenmeyer flask equipped with magnetic stirrer and oil bath for heating is charged with 5.0 g (0.046 mole) of o-aminophenol and 100 ml of dimethylformamide. The charge is stirred to dissolve o-aminophenol and 6.0 g (0.02 mole) of 6-fluoro-2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline (IV) added. The reaction mixture is reacted at 80° to 90° C. for 2 hours to form an organic precipitate; 100 ml of water is added to the warm mixture which is then allowed to cool and placed overnight in a refrigerator to crystallize. The solids are collected, washed with methanol and dried to obtain 7.5 g of brown-tan solid. A solution of the product in 100 ml of dimethylformamide is treated with activated carbon and filtered. A first portion of 75 ml of methanol is added to the warm filtrate then an additional 25 ml portion. Cooling and scratching gives 5.5 g of orange crystals of the purified product.

Workup

  1. customAn Erlenmeyer flask equipped with magnetic stirrer and oil bath
  2. temperaturefor heating
  3. additionadded
  4. customThe reaction mixture is reacted at 80° to 90° C. for 2 hours
  5. customto form an organic precipitate
  6. temperatureto cool
  7. customto crystallize
  8. customThe solids are collected
  9. washwashed with methanol
  10. customdried

Sources & evidence

ORD record
ord-33e279516a4a4bfa94061e28e647544a
Source dataset
uspto-grants-2008_08
Patent number
US07410974B2

Reaction notes

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