Sodium Carbonate → N-(4-Amino-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

HRID 1820119Notes

Reaction equation

HRID 1820119 reaction equation
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-])=O)=[CH:12][C:11]=2[CH3:20])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(O)(=O)C.[Zn]>[NH2:17][C:13]1[CH:12]=[C:11]([CH3:20])[C:10]([NH:9][C:7](=[O:8])[CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:15]([CH3:16])[CH:14]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 687127672-Cyclopentyl-N-(2,6-dimethyl-4-nitro-phenyl)-acetamide

Product 1

HCID 68707920N-(4-Amino-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamideYield 89%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Zinc dust (10 g) was added in portions over 10 minutes to 2-cyclopentyl-N-(2,6-dimethyl-4-nitro-phenyl)-acetamide (1.45 g) in tetrahydrofuran (40 mL) and acetic acid (10 mL) cooled to 0° C. The reaction mixture was stirred 2 hours at 25° C., neutralized with solid sodium carbonate and filtered through silica (50 g), which was washed with ethyl acetate (200 mL). The organic phase was concentrated in vacuo to furnish 1.15 g (89% yield) of the title compound as a light orange solid. 1H NMR (500 MHz, DMSO-d6): 1.20 (m, 2H), 1.51 (m, 2H), 1.60 (m, 2H), 1.75 (m, 2H), 1.96 (s, 6H), 2.22 (m, 1H), 2.23 (d, 2H), 4.81 (b, 2H), 6.23 (s, 2H), 8.74 (s, 1H).

Workup

  1. filtrationfiltered through silica (50 g), which
  2. washwas washed with ethyl acetate (200 mL)
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-6bf21321b3dc4814b1f49a26226fd6f0
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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