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Diisopropylethylamine → [4-(3-Fluoro-4-nitrophenoxy)-7-methoxyquinolin-6-yl]carbamic acid benzyl ester

HRID 853389
Notes
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Reaction equation

HRID 853389 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][C:26]1[CH:27]=[C:28]([OH:35])[CH:29]=[CH:30][C:31]=1[N+:32]([O-:34])=[O:33].C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:35][C:28]1[CH:29]=[CH:30][C:31]([N+:32]([O-:34])=[O:33])=[C:26]([F:25])[CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5209483-Fluoro-4-nitrophenolHCID 58931435(4-Chloro-7-methoxyquinolin-6-yl)carbamic acid benzyl ester

Product 1

HCID 58931261[4-(3-Fluoro-4-nitrophenoxy)-7-methoxyquinolin-6-yl]carbamic acid benzyl esterYield 8.8%

Reagents, catalysts & solvents

1
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

(4-Chloro-7-methoxyquinolin-6-yl)carbamic acid benzyl ester (1.58 g) was added to 1-methyl-2-pyrrolidone (5 ml), and then 3-fluoro-4-nitrophenol (0.87 g) and N,N-diisopropylethylamine (1.2 ml) were added and the mixture was heated and stirred at 130° C. for 6 hours. The reaction solution was poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over magnesium sulfate. The organic layer was concentrated and the obtained residue was subjected to NH silica gel column chromatography for elution with a solvent (ethyl acetate) to obtain the title compound (188 mg) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe organic layer was concentrated
  6. washthe obtained residue was subjected to NH silica gel column chromatography for elution with a solvent (ethyl acetate)

Sources & evidence

ORD record
ord-88878d7c8be8428e862b67100cf2403d
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253286B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes