Hydrochloric Acid → 3-(Azidomethyl)-2-phenylquinoline-4-carboxylic acid

HRID 655910Notes

Reaction equation

HRID 655910 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([O:17]C)=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:2]=[N-:3].O.[OH-].[Li+].Cl>CO.O>[N:1]([CH2:4][C:5]1[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([OH:17])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57893572Methyl 3-(azidomethyl)-2-phenylquinoline-4-carboxylate

Product 1

HCID 578935673-(Azidomethyl)-2-phenylquinoline-4-carboxylic acidYield 78.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(azidomethyl)-2-phenylquinoline-4-carboxylate (2b) (1781 mg, 5.0 mmol) in methanol (50 mL) was added the solution of lithium hydroxide monohydrate (674 mg, 28.1 mmol) in 25 mL water. The reaction mixture was stirred at reflux for 4 h and the residue was acidified with 1 N HCl to pH 2. The volume of reaction mixture was reduced under reduced pressure. The resulting aqueous phase was extracted with ethyl acetate (150 mL). The organic phase was separated and washed with brine (20 ml) and dried over sodium sulfate and then concentrated in vacuo. Crystallization from ethyl acetate/hexane to afford the title compound (1200 mg, 66%) as an off white solid. MS APCI, m/z=305 (M+1). LCMS: 1.09 min.

Workup

  1. temperatureat reflux for 4 h
  2. customThe volume of reaction mixture
  3. extractionThe resulting aqueous phase was extracted with ethyl acetate (150 mL)
  4. customThe organic phase was separated
  5. washwashed with brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-42515479246a419e94e91f0bdb10180e
Source dataset
uspto-grants-2011_12
Patent number
US08071621B2

Reaction notes

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