Lithium hydroxide, monohydrate → 3-((6-Aminopyridin-3-yl)carbamoyl)-4-methylbenzoic acid

HRID 453388Notes

Reaction equation

HRID 453388 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:14]([O:16]C)=[O:15])=[O:10])=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:14]([OH:16])=[O:15])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68453452Methyl 3-((6-aminopyridin-3-yl)carbamoyl)-4-methylbenzoate

Product 1

HCID 593818933-((6-Aminopyridin-3-yl)carbamoyl)-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 3-((6-aminopyridin-3-yl)carbamoyl)-4-methylbenzoate (0.11 g, 0.39 mmol) dissolved in tetrahydrofuran (1.5 mL) was added a solution of lithium hydroxide, monohydrate (24 mg, 0.58 mmol) in water (1.5 mL). The reaction mixture was stirred at RT for 4 h. THF was removed in vacuo and to the aqueous layer was added 2N HCl until pH 4-5. The precipitate formed was collected by filtration, washed with water, dried to give 3-((6-aminopyridin-3-yl)carbamoyl)-4-methylbenzoic acid as a tan solid. MS (ESI, pos. ion) m/z: 272.1 (M+1).

Workup

  1. customTHF was removed in vacuo and to the aqueous layer
  2. additionwas added 2N HCl until pH 4-5
  3. customThe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ab8f7bfd0cd1467e82efd811948087a1
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

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