Water → 4-Chloro-7-methoxyquinoline-6-carboxamide

HRID 1010145Notes

Reaction equation

HRID 1010145 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].O.[NH3:18].O>O1CCCC1>[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]([NH2:18])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 12896473Azane;hydrateHCID 229365757-Methoxy-4-chloro-quinoline-6-carbonyl chloride

Product 1

HCID 229364184-Chloro-7-methoxyquinoline-6-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Methoxy-4-chloroquinoline-6-carbonyl chloride (2.7 g) was dissolved in tetrahydrofuran (150 ml), and the solution was cooled to 0° C. After adding 30% ammonia water (5 ml), the mixture was stirred at room temperature for 30 minutes. Water was added, extraction was performed 3 times with ethyl acetate, and then the organic layers were combined, washed with water and saturated brine, dried over sodium sulfate and dried under reduced pressure to obtain the title compound (1.35 g).

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-77e4c899d10b445a99d22c347db06f12
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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