Hydrochloric Acid → HCID 46872519, compound

HRID 1942277Notes

Reaction equation

HRID 1942277 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]=1/[CH:11]=[CH:10]/[C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:24])=[O:2])=[CH:5][N:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 46872516HCID 46872516, compound

Product 1

HCID 46872519HCID 46872519, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-nicotinic acid methyl ester (150 mg, 0.47 mmol) in THF (1.5 mL) and methanol (0.5 mL) was added a solution of lithium hydroxide monohydrate (39.2 mg, 0.94 mmol) in water (1.5 mL) added and the resulting mixture stirred at room temperature for 1 h. The mixture was acidified to pH 4 with HCl (1 N) and cooled to 0° C. The precipitate was filtered off and dried to afford the title compound (134 mg, 93%) which was obtained as a white solid. MS: m/e=305.4 [M−H]+.

Workup

  1. additionadded
  2. temperaturecooled to 0° C
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-00d697393f2040248c14ee0533921725
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

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