Sodium Bicarbonate → HCID 22724086, compound

HRID 2086816Notes

Reaction equation

HRID 2086816 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[C:14]([NH:18][C:19]3[C:24]([N+:25]([O-])=O)=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:15]=[CH:16][CH:17]=2)=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O1CCOCC1.[Fe]>[NH2:25][C:24]1[C:19]([NH:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:10](=[O:11])[NH:9][C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH:13]=2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 22724030HCID 22724030, compound

Product 1

HCID 22724086HCID 22724086, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[3-(3,5-dichlorophenylcarbamoyl)phenylamino]-3-nitropyridine (565 mg) and iron powder (0.4 g) in acetic acid (5 ml) and 1,4-dioxane (5 ml) was stirred at 80° C. for 3 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 3-amino-2-[3-(3,5-dichlorophenylcarbamoyl)phenylamino]pyridine (284 mg).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-7cdd25399e7a42e09d7f383486d59cd2
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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