HCID 58099972, compound → HCID 58099975, compound

HRID 2171318Notes

Reaction equation

HRID 2171318 reaction equation
[CH:1]1([C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-])=O)=[CH:8][C:7]=2[OH:16])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:13][C:9]1[C:10]([CH3:12])=[CH:11][C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:7]([OH:16])[CH:8]=1

Participants

4

Reactant 1

HCID 58099972HCID 58099972, compound

Product 1

HCID 58099975HCID 58099975, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask charged with 10% Pd/C (16 mg) was evacuated and placed under a N2 atmosphere. To this was added 2-cyclopentyl-4-methyl-5-nitro-phenol (160 mg, 0.72 mmol) as a solution in methanol (3 mL). The reaction mixture was stirred under H2 atmosphere for 4 h, then filtered and concentrated in vacuo to provide 5-amino-2-cyclopentyl-4-methylphenol a light tan solid (130 mg, 94% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 8.47 (s, 1H), 6.60 (s, 1H), 6.08 (s, 1H), 4.44 (s, 2H), 3.02 (dd, J=2.4, 17.2 Hz, 1H), 1.91 (s, 3H), 1.84-1.77 (m, 2H), 1.71-1.66 (m, 2H), 1.58-1.54 (m, 2H), 1.44-1.39 (m, 2H).

Workup

  1. customwas evacuated
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-305ab729deed4f9e9627dd2080f59582
Source dataset
uspto-grants-2015_06
Patent number
US09051324B2

Reaction notes

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