HCID 66728944, compound → 5-(Propan-2-yl)pyridin-3-amine

HRID 1098579Notes

Reaction equation

HRID 1098579 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[N:8][CH:9]=1)[CH3:3]>C(O)C.[Pd]>[CH:2]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[N:8][CH:9]=1)([CH3:3])[CH3:1]

Participants

4

Procedure

To a solution of 5-(prop-1-en-2-yl)pyridin-3-amine (0.773 g, 2.48 mmol) in ethanol (8 mL) was added 10% Pd/C (0.132 g, 0.124 mmol) and the resulting suspension was stirred under a hydrogen atmosphere (1 atm) for 18 h. The reaction was filtered through Celite® and washed forward with EtOH. The filtrate was concentrated, diluted with EtOAc (30 mL) and washed with H2O (1×15 ml) and brine (1×15 ml). The aqueous phase was back-extracted with EtOAc (1×20 ml). The combined organic layers were dried (MgSO4) and concentrated to afford 5-isopropylpyridin-3-amine (0.453 g, 134%) as a light yellow oil. MS (ESI) m/z: 137.1 (M+H+).

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. washwashed forward with EtOH
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with EtOAc (30 mL)
  5. washwashed with H2O (1×15 ml) and brine (1×15 ml)
  6. extractionThe aqueous phase was back-extracted with EtOAc (1×20 ml)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-132e49140dad42fab7c464c6af402992
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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