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Water → 4-chloro-7-methoxy-N-methylquinoline-6-carboxamide

HRID 1433597
Notes
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Reaction equation

HRID 1433597 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:14](Cl)=[O:15].COC1C=C2C(C(=O)C=[CH:25][NH:26]2)=CC=1C(O)=O.CN.O>O1CCCC1>[CH3:25][NH:26][C:14]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[N:10]=[CH:9][CH:8]=[C:7]2[Cl:13])=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 229364397-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acidHCID 229365757-Methoxy-4-chloro-quinoline-6-carbonyl chloride

Product 1

HCID 589309334-chloro-7-methoxy-N-methylquinoline-6-carboxamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

After dissolving 7-methoxy-4-chloro-quinoline-6-carbonyl chloride synthesized by the method of Production Example 152-2 from 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (947 mg) in tetrahydrofuran (70 ml), the solution was cooled to 0° C. A 40% aqueous methylamine solution (0.4 ml) was added, and the mixture was stirred at room temperature for 30 minutes. Water was added, extraction was performed 3 times with ethyl acetate, and the organic layers were combined, washed with water and saturated brine, dried over sodium sulfate and then dried under reduced pressure to obtain the title compound (710 mg).

Workup

  1. extractionextraction
  2. washwashed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4d0cda006ff843aebdfd997306905783
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