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Water → 8-benzyloxy-5-(2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one

HRID 969455
Notes
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Reaction equation

HRID 969455 reaction equation
[BH4-].[Li+].[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:22](=[O:25])[CH2:23][Cl:24])=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[CH:17]=[CH:16]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ClCCl.O>C1COCC1>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:22]([OH:25])[CH2:23][Cl:24])=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[CH:17]=[CH:16]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4148881Lithium borohydrideHCID 109035505-(2-chloroacetyl)-8-phenylmethoxy-1H-quinolin-2-one

Product 1

HCID 224992458-benzyloxy-5-(2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

238 mL of a 2 molar solution of lithium borohydride in THF are added dropwise to 52 g (159 mmol) 8-benzyloxy-5-(2-chloro-acetyl)-1H-quinolin-2-one in 650 mL THF at 0° C. It is stirred for two hours at 0° C., then heated to ambient temperature, combined with 200 mL dichloromethane and 75 mL water and stirred for a further hour. The precipitated solid is suction filtered and the organic phase of the filtrate is separated off and freed from the solvent. The residue is combined with the solid from the preceding filtration and repeatedly stirred with diethyl ether and THF. Yield: 51.6 g (99%); mass spectroscopy [M+H]+=330/32.

Workup

  1. temperatureheated to ambient temperature
  2. stirringstirred for a further hour
  3. filtrationfiltered
  4. customthe organic phase of the filtrate is separated off
  5. filtrationThe residue is combined with the solid from the preceding filtration
  6. stirringrepeatedly stirred with diethyl ether and THF

Sources & evidence

ORD record
ord-88314aa98dbd4c2088823ca21dc1d30d
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07307076B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes