Formic Acid → HCID 18796728, compound

HRID 1900671Notes

Reaction equation

HRID 1900671 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.Cl.[NH2:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:16][NH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=2)[N:21]=[CH:20][N:19]=1>O>[CH:1]([NH:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:16][NH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=2)[N:21]=[CH:20][N:19]=1)=[O:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 18796654HCID 18796654, compound

Product 1

HCID 18796728HCID 18796728, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1 g of powdered iron was added in portions to a mixture comprising 1 g of 4-(3-nitro-4-methoxybenzyl)amino-6-chloroguinazoline, 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-(8-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 180 mg of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. temperatureimmediately cooled with ice
  3. customThe obtained mixture was reacted at that temperature for one hour and at room temperature for one hour
  4. customThe crystals thus formed
  5. filtrationwere recovered by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-042c330677774a748d79c8c83456b53c
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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