3-(Benzyloxy)-5-phenylpyridin-2-amine → 2-Amino-5-phenylpyridin-3-ol

HRID 425883Notes

Reaction equation

HRID 425883 reaction equation
C([O:8][C:9]1[C:10]([NH2:21])=[N:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:21][C:10]1[C:9]([OH:8])=[CH:14][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][N:11]=1

Participants

4

Reactant 1

HCID 103787373-(Benzyloxy)-5-phenylpyridin-2-amine

Product 1

HCID 211113862-Amino-5-phenylpyridin-3-olYield 93%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-benzyloxy-5-phenyl-pyridin-2-ylamine (Example I-87, 3.27 g, 11.8 mmol) in methanol (30 mL) was added Pd(OH)2 (2.5 g, 2.37 mmol). The mixture was degassed and charged with hydrogen three times, and then stirred under hydrogen balloon for 5 hr. The reaction was filtered through a celite pad, washed with methanol, and condensed. After high vacuum dry, 2-amino-5-phenyl-pyridin-3-ol was obtained (2.04 g, 93% yield). MS m/z 187 [M+1].

Workup

  1. customThe mixture was degassed
  2. additioncharged with hydrogen three times
  3. filtrationThe reaction was filtered through a celite pad
  4. washwashed with methanol, and condensed
  5. customAfter high vacuum dry

Sources & evidence

ORD record
ord-ab4149d663924edd936dcfea7374d436
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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