HCID 22321883, compound → HCID 22321920, compound

HRID 496643Notes

Reaction equation

HRID 496643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[NH2:20][C:17]1[CH:18]=[CH:19][C:10]([CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 1

HCID 22321883HCID 22321883, compound

Product 1

HCID 22321920HCID 22321920, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of compound 74 (29 g), 10% Pd/C (3 g), and ethyl acetate (400 ml) was stirred under an hydrogen atmosphere for 6 hours. The catalyst was removed by filtration and replaced by fresh catalyst (3 g). The hydrogenation was then continued for another 16 hours, the catalyst was again filtered off, the filtrate evaporated to dryness and the residue treated with iso-hexane to give a white precipitate which was isolated by filtration and dried to give compound 75 (23.5 g).

Workup

  1. customThe catalyst was removed by filtration
  2. waitThe hydrogenation was then continued for another 16 hours
  3. filtrationthe catalyst was again filtered off
  4. customthe filtrate evaporated to dryness
  5. additionthe residue treated with iso-hexane
  6. customto give a white precipitate which
  7. customwas isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-a2d0345f9fea4050a1260f4091ec31b8
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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