Sodium Carbonate → HCID 11609103, compound

HRID 1820142Notes

Reaction equation

HRID 1820142 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH:11][C:12](=[O:18])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:4]([CH3:19])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(O)(=O)C.[Zn]>[NH2:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([CH3:19])[C:5]=1[NH:11][C:12](=[O:18])[CH2:13][C:14]([CH3:16])([CH3:15])[CH3:17]

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 68707090HCID 68707090, compound

Product 1

HCID 11609103HCID 11609103, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Zinc dust (16 g) was added in portions over 2 hours to N-(4-bromo-2-methyl-6-nitro-phenyl)-3,3-dimethyl-butyramide (2.74 g) in tetrahydrofuran (50 mL) and acetic acid (12 mL) cooled to 0° C., and then stirred 30 minutes at 25° C. The reaction mixture was poured into a suspension of sodium carbonate (16 g) in tetrahydrofuran and filtered through silica (50 g), which was washed with ethyl acetate (100 mL). The organic phase was concentrated in vacuo to furnish 2.47 g (100% yield) of the title compound as a pale red solid. LC-MS (m/z) 300 (MH+); tR=2.54, (UV, ELSD) 96%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.04 (s, 9H), 2.05 (s, 3H), 2.21 (s, 2H), 4.94 (s, 2H), 6.59 (d, 1H), 6.74 (d, 1H), 8.85 (s, 1H).

Workup

  1. filtrationfiltered through silica (50 g), which
  2. washwas washed with ethyl acetate (100 mL)
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-0f6ef7153c1942eda14bb36e162c66f5
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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