Sodium Carbonate → HCID 22145850, compound

HRID 1383474Notes

Reaction equation

HRID 1383474 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, compound

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

Sources & evidence

ORD record
ord-435f5c08e74e43e691345c3413f34146
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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