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Benzyl Alcohol → (7-Methoxy-4-oxo-1,4-dihydroquinolin-6-yl)carbamic acid benzyl ester

HRID 1433518
Notes
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Reaction equation

HRID 1433518 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[CH:8]=[CH:9][NH:10]2)=[CH:5][C:4]=1C(O)=O.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C>CN(C)C=O.[Cl-].[Na+].O>[CH2:17]([O:24][C:47](=[O:32])[NH:44][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[NH:10][CH:9]=[CH:8][C:7]2=[O:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 229364397-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid

Product 1

HCID 58931364(7-Methoxy-4-oxo-1,4-dihydroquinolin-6-yl)carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
95 °C

Procedure

After dissolving 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (2.58 g) in N,N-dimethylformamide (50 ml), there were added benzyl alcohol (3.29 ml), diphenylphosphoryl azide 2.51 ml) and triethylamine (1.63 ml), and the mixture was heated and stirred at 95° C. for 5 hours. The reaction solution was poured into saturated brine and extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate and concentrated. The obtained residue was subjected to NH silica gel column chromatography and eluted with a solvent (ethyl acetate:methanol=5:1) to obtain the title compound (2.03 g) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with a solvent (ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-bc5f36e2c0fd473e9721a012439f8a87
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612092B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes