Acetic Acid → HCID 18796654, compound

HRID 1938534Notes

Reaction equation

HRID 1938534 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[N:12]=[CH:11][N:10]=1)([O-])=O.C(O)(=O)C.O>[Fe].C(O)C>[ClH:19].[NH2:1][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 54546096HCID 54546096, compound

Product 1

HCID 18796654HCID 18796654, compoundYield 215.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

1 g of powdered iron was added in portions to a mixture comprising 1 g of 4-(3-nitro-4-methoxybenzyl)amino-6-chloroquinazoline, 4 ml of acetic acid, 4 ml of water and 40 ml of ethanol, while heating the mixture under mild reflux. The obtained mixture was heated under reflux for 2 hours and filtered to remove insolubles. Concentrated hydrochloric acid was added in portions to the brown filtrate obtained above to give a yellow transparent solution. This solution was cooled with ice to precipitate crystals. The crystals were recovered by filtration and dried to give 1.1 g of 4-(3-amino-4-methoxybenzyl)amino-6-chloroquinazoline hydrochloride. This hydrochloride was dissolved in ethanol/water and the obtained solution was made alkaline by adding a 15% aqueous solution of sodium hydroxide in portions. Water was added to the resulting alkaline solution in portions to precipitate crystals. The crystals were recovered by filtration, washed with water and dried to give 770 mg of 4-(3-amino-4-methoxybenzyl)amine-6-chloroquinazoline (an aniline derivative), Separately. 1 ml of formic acid was dropped into 2 ml of acetic anhydride under cooling with ice and the obtained mixture was heated at 50° C. for 15 minutes and immediately cooled with ice, followed by the addition of the above aniline derivative as such (in a crystalline state), The obtained mixture was reacted at that temperature for one hour and at room temperature for one hour, followed by the addition of water. The crystals thus formed were recovered by filtration, washed with water and dried to give 130 mg of the title compound.

Workup

  1. temperaturewhile heating the mixture under mild reflux
  2. temperatureThe obtained mixture was heated
  3. temperatureunder reflux for 2 hours
  4. filtrationfiltered
  5. customto remove insolubles
  6. additionConcentrated hydrochloric acid was added in portions to the brown filtrate
  7. customobtained above
  8. customto give a yellow transparent solution
  9. temperatureThis solution was cooled with ice
  10. customto precipitate crystals
  11. filtrationThe crystals were recovered by filtration
  12. customdried

Sources & evidence

ORD record
ord-91588cc0b6a3422aad8d450b49cd5b0c
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Reaction notes

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