Sodium Carbonate → HCID 22145850, compound

HRID 1994314Notes

Reaction equation

HRID 1994314 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[NH:12][C:13](=[O:28])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:11])[C:3]=1[NH:12][C:13](=[O:28])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)[CH:15]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 22145772HCID 22145772, compound

Product 1

HCID 22145850HCID 22145850, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of N-(2,6-dichloro-4-nitrophenyl)-3-cyclopentyloxy-4-methoxybenzamide (1.5 g) in glacial acetic acid (22 mL) is treated with iron pin dust (1.3 g) and the mixture is heated with stirring at 90° C. for 1 hour. The reaction mixture is cooled, basified to pH 8 by treatment with saturated aqueous sodium carbonate solution, and extracted with ethyl acetate (2×150 mL). The combined organic extract is dried over magnesium sulfate and concentrated in vacuo, to give a white solid. This solid is subjected to flash chromatography, eluting with a mixture of ethyl acetate and pentane (1:1 v/v), to give N-(2,6-dichloro-4-aminophenyl)-3-cyclopentyloxy-4-methoxybenzamide (0.8 g), m.p. 170-172° C. [Elemental analysis: C, 54.8; H, 5.04; N, 6.5; Cl, 17.4%. calculated: C, 57.7; H, 5.1; N, 7.1; Cl, 17.9%].

Workup

  1. temperaturethe mixture is heated
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. extractionThe combined organic extract
  5. dry with materialis dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a white solid
  8. washeluting with a mixture of ethyl acetate and pentane (1:1 v/v)

Sources & evidence

ORD record
ord-ddd2942bd29c457694b97a600b352398
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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