Ammonia → (4-Amino-2,6-dimethyl-phenyl)-carbamic acid propyl ester

HRID 1820124Notes

Reaction equation

HRID 1820124 reaction equation
Cl.[CH2:2]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][C:9]=1[CH3:18])[CH2:3][CH3:4].N>O1CCCC1.[Zn]>[CH2:2]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:9]([CH3:18])=[CH:10][C:11]([NH2:15])=[CH:12][C:13]=1[CH3:14])[CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 68709792(2,6-Dimethyl-4-nitro-phenyl)-carbamic acid propyl ester

Product 1

HCID 68707091(4-Amino-2,6-dimethyl-phenyl)-carbamic acid propyl esterYield 99.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Aqueous hydrochloric acid (6 M, 8.3 mL) was added slowly to a mixture of zinc dust (4.9 g) and (2,6-dimethyl-4-nitro-phenyl)-carbamic acid propyl ester (1.26 g) in tetrahydrofuran (50 mL) cooled to 0° C. The reaction mixture was then stirred for 5 hours at 25° C., and the pH adjusted to 10 with 25% aqueous ammonia. The product was extracted with ethyl acetate (3×50 mL), the combined organic phases were dried over magnesium sulfate and concentrated in vacuo to furnish 1.1 g (99% yield) of the title compound as a dark oil. The crude product was used without further purification. 1H NMR (500 MHz, DMSO-d6): 0.91 (t, 3H), 1.60 (m, 2H), 1.99 (s, 6H), 3.95 (t, 2H), 4.82 (s, 2H), 6.23 (s, 2H), 8.14 (s, 1H).

Workup

  1. extractionThe product was extracted with ethyl acetate (3×50 mL)
  2. dry with materialthe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ced9ad4ccedd43e296401dd04201bcf0
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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