Methane → HCID 178496764, compound

HRID 1855935Notes

Reaction equation

HRID 1855935 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:6][NH:7][C:8]([C:10]1[O:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)=[CH:13][CH:14]=1)=[NH:9].C(O)C.C>[Pd].CO>[CH3:10][O-:11].[ClH:2].[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[O:11][C:10]([C:8](=[NH:9])[NH:7][CH2:6][C:5]2[CH:24]=[CH:25][C:26]([Cl:27])=[C:3]([Cl:2])[CH:4]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 702EthanolHCID 178479329HCID 178479329, compound

Product 1

HCID 178496764HCID 178496764, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of the compound of Example I (31 g, 0.073 mole), ethanol (350 ml) and 5% Pd/C-50% H2O (1.5 g) was subjected to hydrogenation for 5 hours at room temperature, using 14.0 psia H2 (theory: 14.7 psia). Methanol (1000 ml) was added to the reaction mixture. The mixture was heated, treated with Darco, filtered, and the filtrate was reduced in volume to 400 ml under reduced pressure. The mixture was cooled and the product was collected by filtration. The product was recrystallized from methanol: m.p. 225°-257°, yield: 10 g (34%).

Workup

  1. temperatureThe mixture was heated
  2. filtrationfiltered
  3. temperatureThe mixture was cooled
  4. filtrationthe product was collected by filtration
  5. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-fab179b1e3f6400c97d9fdacb6effe7a
Source dataset
uspto-grants-1980_08
Patent number
US04217286

Reaction notes

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