HCID 20311787, compound → HCID 20311789, compound

HRID 2420459Notes

Reaction equation

HRID 2420459 reaction equation
[O:1]=[C:2]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]2[C:4]([C:5]([N+:17]([O-])=O)=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[H][H]>[Pd].O1CCCC1>[O:1]=[C:2]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]2[C:4]([C:5]([NH2:17])=[CH:6][CH:7]=[CH:8]2)=[N:3]1

Participants

5

Reactant 2

HCID 20311787HCID 20311787, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20311789HCID 20311789, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Two and one half grams of 2-oxo-3-phenyl-7-nitroindole were dissolved in 200 ml. of THF (tetrahydrofuran). Two grams of 5% palladium-on-carbon were added and the mixture placed in a low pressure hydrogenation apparatus at 60 psi of hydrogen. After 18 hours, the theoretical amount of hydrogen had been absorbed. The hydrogenation mixture was filtered to remove the catalyst and the filtrate was evaporated to dryness in vacuo. The residue containing the 2-oxo-3-phenyl-7-aminoindole formed in the above hydrogenation melted at 226°-30° C. after recrystallization from methanol; yield = 1.5 g.

Workup

  1. customthe theoretical amount of hydrogen had been absorbed
  2. filtrationThe hydrogenation mixture was filtered
  3. customto remove the catalyst
  4. customthe filtrate was evaporated to dryness in vacuo
  5. additionThe residue containing the 2-oxo-3-phenyl-7-aminoindole
  6. customformed in the above hydrogenation melted at 226°-30° C.
  7. customafter recrystallization from methanol

Sources & evidence

ORD record
ord-adbf36d448b5472fa29cf8313121253b
Source dataset
uspto-grants-1978_08
Patent number
US04110465

Reaction notes

Loading…