2-Hydroxy-6-chloroquinoxaline → 6-chloro-3,4-dihydroquinoxalin-2(1h)-one

HRID 1378728

Reaction equation

HRID 1378728 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[N:7]2>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][NH:7]2

Participants

4

Reactant 2

HCID 755072-Hydroxy-6-chloroquinoxalineHCID 4311764Sodium borohydride

Product 1

HCID 2835276-chloro-3,4-dihydroquinoxalin-2(1h)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (5.10 g) is added to a mixture of 6-chloro-1,2-dihydroquinoxalin-2-one (5.60 g), and ethanol (200 ml). The resultant solution is stirred for 2.5 hr at 20°-25°. The material is partitioned between water and ethyl acetate, the phases are separated, the organic phase is dried over magnesium sulfate and concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane to give the title compound, mp 171°-174°; IR (mineral oil) 2953, 2925, 1687, 1517, 1408, 1307 and 1299 cm-1 ; NMR (CDCl3 -MeOD) 6.6-6.8 and 3.95 δ; MS (m/z) 182, 153.

Workup

  1. customThe material is partitioned between water and ethyl acetate
  2. customthe phases are separated
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a solid which
  6. customis recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f7e7c2d8e1cb4d019ba2b747b8d2818e
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Linked notes

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