Ammonium formate → HCID 23298118, compound

HRID 1953414Notes

Reaction equation

HRID 1953414 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:10]=[C:11](/[CH:15]=[CH:16]/[C:17]3[CH:18]=[C:19]([NH:23][C:24]4[C:29]([N+:30]([O-])=O)=[CH:28][CH:27]=[CH:26][N:25]=4)[CH:20]=[CH:21][CH:22]=3)[CH:12]=[N:13][CH:14]=2)=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>C(O)C.O.[Fe]>[NH2:30][C:29]1[C:24]([NH:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17](/[CH:16]=[CH:15]/[C:11]3[CH:12]=[N:13][CH:14]=[C:9](/[CH:8]=[CH:7]/[C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH:10]=3)[CH:18]=2)=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 232981352-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenylamino]-3-nitropyridine

Product 1

HCID 23298118HCID 23298118, compoundYield 87.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenylamino]-3-nitropyridine (331 mg), iron powder (132 mg) and ammonium formate (297 mg) in ethanol (6 ml) and water (2 ml) was stirred at 90pbC. for 30 minutes. The mixture was filtered while hot. The filtrate was added to aqueous sodium bicarbonate solution and extracted with ethyl acetate twice. The combined organic solution was washed with sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was washed with diisopropyl ether to give 3-amino-2-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenylamino]pyridine (270 mg).

Workup

  1. filtrationThe mixture was filtered while hot
  2. additionThe filtrate was added to aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate twice
  4. washThe combined organic solution was washed with sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washThe resultant solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-49dd5a2c97c44de0bc0c6fdbdba5934f
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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