Ethylenediamine → 6-(Cyclopropylmethoxy)pyridin-3-amine

HRID 1898317Notes

Reaction equation

HRID 1898317 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=2)[CH2:3][CH2:2]1.C(N)CN>C(O)C.[Pd]>[CH:1]1([CH2:4][O:5][C:6]2[N:7]=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 675034292-(Cyclopropylmethoxy)-5-nitropyridine

Product 1

HCID 284136536-(Cyclopropylmethoxy)pyridin-3-amineYield 23.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(cyclopropylmethoxy)-5-nitropyridine (2.0 g) in ethanol (10.0 mL) was added Pd/C (0.500 g) and ethylene diamine (5.0 mL). The reaction mixture was subjected for hydrogenation in Parr apparatus under 40 psi for 2-3 h. The reaction mass was quenched in water and extracted with DCM and concentrated the organic layer to afford 0.400 g of the desired product. 1HNMR (CDCl3): δ 0.31-0.32 (m, 2H), 0.43-0.46 (m, 2H), 1.07-1.12 (m, 1H), 3.62 (d, J=6.6 Hz, 2H), 4.25 (s, 2H), 6.24 (d, J=6.6 Hz, 1H), 6.89 (s, 1H), 7.05 (dd, J=3.0 Hz & 2.4 Hz, 1H); MS [M+H]+: 165.13.

Workup

  1. customThe reaction mass was quenched in water
  2. extractionextracted with DCM
  3. concentrationconcentrated the organic layer

Sources & evidence

ORD record
ord-23ea2edcd9ef43e29b4264953458c8f2
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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