Dichloromethane → HCID 22504090, compound

HRID 1814318Notes

Reaction equation

HRID 1814318 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>C1COCC1.[Ni]>[CH2:1]([O:8][C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 22504065HCID 22504065, compound

Product 1

HCID 22504090HCID 22504090, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Benzyloxy-6-methoxy-3 nitro-pyridine (3.41 g, 13.1 mmol) was shaken with 1 g Rainey nickel in 100 mL THF in a Parr hydrogenation apparatus at 48 psi H2 for 20 h. TLC analysis (silica, CH2Cl2) indicated complete consumption of starting material. The reaction mixture was filtered and concentrated. The crude product was purified by gradient elution flash chromatography (SiO2, 1:1 CH2Cl2/hexanes to 3:1 CH2Cl2/hexanes to 100% CH2Cl2) to give 1.65 g (7.17 mmol, 55%) of 2-benzyloxy-6-methoxy-pyridin-3-ylamine. MS (APCI) m/z 231.2 (M+1). 1H NMR (300 MHz) CDCl3 7.29-7.48 (m, 5H), 6.98 (d, J=8.1 Hz, 1H), 6.19 (d, J=8.1 Hz, 1H), 5.42 (s, 2H), 3.84 (s, 3H).

Workup

  1. customconsumption of starting material
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customThe crude product was purified by gradient elution flash chromatography (SiO2, 1:1 CH2Cl2/hexanes to 3:1 CH2Cl2/hexanes to 100% CH2Cl2)

Sources & evidence

ORD record
ord-74ae73a76d94424a9588280b897b5bf3
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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