Hydrochloric Acid → Methyl 2-amino-5-fluoroisonicotinate

HRID 1802181Notes

Reaction equation

HRID 1802181 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:16]([F:19])=[CH:17][N:18]=1)[C:12]([O:14][CH3:15])=[O:13])=O)(C)(C)C.Cl>>[NH2:8][C:9]1[CH:10]=[C:11]([C:16]([F:19])=[CH:17][N:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67776932Methyl 2-((tert-butoxycarbonyl)amino)-5-fluoroisonicotinate

Product 1

HCID 67777217Methyl 2-amino-5-fluoroisonicotinateYield 82.2%

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 2-(tert-butoxycarbonylamino)-5-fluoroisonicotinate (1.80 g, 6.66 mmol) and hydrochloric acid (6N in ether, 40 ml, 240 mmol) is stirred for 20 hours at 25° C. The solvent is evaporated and the light brown slurry is diluted with ethyl acetate, cooled to 0° C. and adjusted to pH 8 with sat. aqueous sodium carbonate solution. The organic layer is washed with brine, dried with magnesium sulfate and the solvent is removed under reduced pressure affording methyl 2-amino-5-fluoroisonicotinate (932 mg, 82.2%) as a brown waxy solid. MS: m/z=171.0 (M+H+).

Workup

  1. customThe solvent is evaporated
  2. additionthe light brown slurry is diluted with ethyl acetate
  3. temperaturecooled to 0° C.
  4. washThe organic layer is washed with brine
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b9c3b27add114eac9405dc262a06f3a8
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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