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Ammonium formate → 2-isopropoxypyridin-3-amine

HRID 450561
Notes
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Reaction equation

HRID 450561 reaction equation
[CH:1]([O:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH:1]([O:4][C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 696692682-(1-Methylethoxy)-3-nitropyridine

Product 1

HCID 218508472-isopropoxypyridin-3-amine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Palladium hydroxide on carbon (20%, 0.076 g, 0.54 mmol) was added into a solution of 2-iso-propoxy-3-nitro-pyridine (1.97 g, 10.8 mmol) and ammonium formate (3.40 g, 54.0 mmol) in ethanol (100 mL) at ambient temperature. The solution was stirred for 2 hours at 90° C., cooled to ambient temperature, filtered through Celite and washed with MeOH. The filtrate was concentrated in vacuo and triturated from diethyl ether to yield brown oil which was used in the next step without further purification.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered through Celite
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customtriturated from diethyl ether
  6. customto yield brown oil which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-38b385b86d064a22905507dafa8eb245
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486953B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes