Dichloromethane → HCID 22504041, compound

HRID 1814292Notes

Reaction equation

HRID 1814292 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:12][CH:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O)[CH3:14].C(Cl)Cl>C1COCC1.[Ni]>[CH3:14][CH:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22])[CH2:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 22504165HCID 22504165, compound

Product 1

HCID 22504041HCID 22504041, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-1-[2-(2-nitro-phenoxy)-propyl]-naphthalene (1.51 g, 4.70 mmol) was shaken with Rainey nickel (0.5 g) in THF (50 mL) at 49.0 psi H2 for 5.4 hours. TLC analysis (silica, CH2Cl2) indicated complete consumption of starting material. The reaction mixture was filtered and concentrated to give 2-[1-methyl-2-(2-methyl-naphthalen-1-yl)-ethoxy]-phenylamine in quantitative yield. MS (APCI) m/z 292.1 (M+H).

Workup

  1. customconsumption of starting material
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-025e0797b2f94075849086e277b42e8a
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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