2-Aminophenol → 2-({2-[2-(5-Nitrofuran-2-yl)ethenyl]quinazolin-4-yl}amino)phenol

HRID 1282932Notes

Reaction equation

HRID 1282932 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].CN(C)C=O.[N+:14]([C:17]1[O:21][C:20]([CH:22]=[CH:23][C:24]2[N:33]=[C:32](Cl)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]>O>[N+:14]([C:17]1[O:21][C:20]([CH:22]=[CH:23][C:24]2[N:33]=[C:32]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[OH:8])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 58012-Aminophenol2×HCID 6228DimethylformamideHCID 536340792-[2-(5-Nitro-2-furyl)vinyl]-4-chloroquinazoline

Product 1

HCID 537632462-({2-[2-(5-Nitrofuran-2-yl)ethenyl]quinazolin-4-yl}amino)phenolYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An Erlenmeyer flask equipped with magnetic stirrer and oil bath for heating was charged with 5.0 g (0.046 mole) of o-aminophenol and 100 ml of dimethylformamide. The charge was stirred to dissolve o-aminophenol and 6.0 g (0.02 mole) of 2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline (IV) added. The reaction mixture was reacted at 80° to 90°C for 2 hours to form an orange precipitate; 100 ml of water was added to the warm mixture which was then allowed to cool and placed overnight in a refrigerator to crystallize. The solids were collected, washed with methanol and dried to obtain 7.5 g of brown-tan solid which melted 224°-6°C with decomposition. A solution of the product in 100 ml of dimethylformamide was treated with activated carbon and filtered. A first portion of 75 ml of methanol was added to the warm filtrate then an additional 25 ml portion. Cooling and scratching gave 5.5 g of orange crystals of the purified product which melted at 230°-1°C with decomposition.

Workup

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

Sources & evidence

ORD record
ord-e7c707f2f8c548c995f3fdf6ad63dace
Source dataset
uspto-grants-1976_08
Patent number
US03973021

Reaction notes

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