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

HRID 387758Notes

Reaction equation

HRID 387758 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 saline, 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 saline
  3. dry with materialdried over sodium sulfate
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-3aa5042b0f304b478da8b78977781bca
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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