HCID 22116147, compound → HCID 22116138, compound

HRID 1276341Notes

Reaction equation

HRID 1276341 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:5]([OH:16])=[C:4]([N+:17]([O-])=O)[CH:3]=1>[Ni].O.CCOC(C)=O>[NH2:17][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:5]=1[OH:16]

Participants

5

Reactant 1

HCID 22116147HCID 22116147, compound

Product 1

HCID 22116138HCID 22116138, compoundYield 100.8%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

To a vigorously stirred suspension of Raney Nickel (3.5 g of a 50% slurry in water, washed with ethanol then EtOAc) in EtOAc (20 ml) is added 4-chloro-2-nitro-6-[2-(pyridin-2-yl)ethyl]phenol (2.09 g, 7.50 mmole) in EtOAc (10 ml). The solution is stirred vigorously overnight under an atmosphere of hydrogen. After this time no starting material is visible by TLC analysis. The solution is decanted from the Raney Nickel. The Raney Nickel was washed several times with EtOAc and the washings combined with the reaction mixture solution. Concentration in vacuo yielded a brown oil which is purified by flash chromatography (SiO2 ; 30% EtOAc in hexane) to yield a pale orange oil (1.88 g, 100%). This was recrystallised from EtOAc/pentane to give the title compound as a pale yellow crystalline solid (1.55 g, 83%), m.p. 91-92° C. dH (250 MHz, CDCl3) 11.5 (bs, 1H), 8.49 (dd, J=5.6, 2.0 Hz, 1H), 7.63 (dt, J=7.7, 1.7 Hz, 1H ), 7.20-7.16 (m, 2H), 6.54 (d, J=2.5 Hz, 2H), 3.84 (bs, 2H ), 3.30-3.25 (m, 2H ), 3.06-3.02 (m, 2H).

Workup

  1. washwashed with ethanol
  2. customThe solution is decanted from the Raney Nickel
  3. washThe Raney Nickel was washed several times with EtOAc
  4. concentrationConcentration in vacuo
  5. customyielded a brown oil which
  6. customis purified by flash chromatography (SiO2 ; 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-981729b8662c49cda2cc85f0fd4c089b
Source dataset
uspto-grants-2000_12
Patent number
US06166041

Reaction notes

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