Ethanol → 4-(alpha-Hydroxymethyl-3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

HRID 2392867Notes

Reaction equation

HRID 2392867 reaction equation
C(O)C.[BH4-].[Na+].C([O:8][C:9]([CH:11]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)=O)C>O>[OH:8][CH2:9][CH:11]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 18796707HCID 18796707, compound

Product 1

HCID 187967884-(alpha-Hydroxymethyl-3,4-methylenedioxybenzyl)amino-6-chloroquinazolineYield 16.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of ethanol and 197 mg of sodium borohydride were added to 200 mg of 4-(α-ethoxycarbonyl-3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. The obtained mixture was refluxed for 30 minutes, followed by the addition of 5 ml of water. The obtained mixture was concentrated under a reduced pressure, followed by the addition of 10 ml of water. The crystal thus precipitated was recovered by filtration. Thus, 30 mg of the title compound was obtained.

Workup

  1. temperatureThe obtained mixture was refluxed for 30 minutes
  2. concentrationThe obtained mixture was concentrated under a reduced pressure
  3. additionfollowed by the addition of 10 ml of water
  4. customThe crystal thus precipitated
  5. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-f56050e9092f4fa6b642805d6aa1c89d
Source dataset
uspto-grants-1998_09
Patent number
US05801180

Reaction notes

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