Hydrochloric Acid → HCID 12069380, compound

HRID 131544Notes

Reaction equation

HRID 131544 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=1)=[CH:13][C:12]([C:27]#[N:28])=[CH:11][CH:10]=2)=[O:5])C.C1COCC1.[OH-].[Na+].Cl>C(O)C.CO>[Cl:26][C:20]1[CH:19]=[C:18]([CH2:17][NH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:27]#[N:28])[CH:13]=3)[N:8]=[CH:7][C:6]=2[C:4]([OH:5])=[O:3])[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10294138HCID 10294138, compound

Product 1

HCID 12069380HCID 12069380, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 8.0 g (20 mmol) 4-(3-Chloro-4-methoxyphenylmethylamino)-6-cyanoquinoline-3-carboxylic acid ethyl ester was added 100 mL THF, 100 mL MeOH and 100 mL 1M NaOH, and the resulting mixture was stirred well. The solids gradually dissolved as the reaction progressed. After 1 h, the THF and most of the MeOH was evaporated under reduced pressure to leave an aqueous slurry of a white solid. The slurry was acidified to pH 1.5 with HCl, stirred well for 1 h, and then filtered and washed well with water to give 7.5 g (20 mmol, 100% yield) of a white chalky solid. Codistilling twice to dryness with absolute ethanol afforded the title compound: LC/MS: M/Z 368 (M+H) observed, 90+% purity; mp: decomposed 255-260° C. LC 2.93°.

Workup

  1. dissolutionThe solids gradually dissolved as the reaction
  2. customthe THF and most of the MeOH was evaporated under reduced pressure
  3. customto leave an aqueous slurry of a white solid
  4. stirringstirred well for 1 h
  5. filtrationfiltered
  6. washwashed well with water
  7. customto give 7.5 g (20 mmol, 100% yield) of a white chalky solid

Sources & evidence

ORD record
ord-5bfe92dd31374117a6e5dbcb3c80f3c1
Source dataset
uspto-grants-2008_06
Patent number
US07384958B2

Reaction notes

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