Sodium Hydroxide → 6-(Benzyloxy)pyridin-3-amine

HRID 1173444Notes

Reaction equation

HRID 1173444 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH:9]=1)([O-])=O.[OH-].[Na+]>CO.O.CC(O)=O.[Fe]>[C:12]1([CH2:11][O:10][C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2956762-benzyloxy-5-nitro-pyridine

Product 1

HCID 5632866-(Benzyloxy)pyridin-3-amineYield 82.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 86607755Acetic acid methanol waterSolvent

Procedure

To a slurry of iron powder (5.32 g, 95 mmol) in MeOH/H2O/HOAc (7.5 mL/7.5 mL/0.30 mL) at 75° C. was added 5-nitro-2-[(phenylmethyl)oxy]pyridine (3.10 g, 13.4 mmol; step A above), portionwise over 20 min. After 2 h, the mixture was cooled, 1M NaOH (10 mL) was added. The mixture was filtered through Celite (MeOH wash×2) and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 2.21 g of the title compound as an orange syrup: MS (ESI) m/z 201 (M+1).

Workup

  1. waitAfter 2 h
  2. temperaturethe mixture was cooled
  3. filtrationThe mixture was filtered through Celite (MeOH wash×2)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-0a053fe48fc34b36974b67f0e9eba061
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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