Hydrochloric Acid → HCID 12069380, compound

HRID 2308231Notes

Reaction equation

HRID 2308231 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-260058984a1f4303b0c7a3c10ce4db74
Source dataset
uspto-grants-2004_12
Patent number
US06835737B2

Reaction notes

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