Ethanol → HCID 178511970, compound

HRID 1762485Notes

Reaction equation

HRID 1762485 reaction equation
[C:1]([O:4]CC)(=[O:3])[CH3:2].[NH2:7][C:8](=[N:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][NH:20]C(=O)[O:22][CH2:23][C:24]1C=CC=CC=1.C([OH:40])C>[Pd]>[C:23]([OH:40])(=[O:22])/[CH:24]=[CH:2]\[C:1]([OH:4])=[O:3].[NH2:20][CH2:19][CH2:18][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([C:8](=[NH:7])[NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:10]=2)[NH:14][CH:13]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 86743053HCID 86743053, compound

Product 1

HCID 178511970HCID 178511970, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The product of Stage (i) (0.8 g) was stirred in ethanol (50 ml) under a hydrogen atmosphere and over 10% palladium on carbon catalyst (0.8, 50% aqueous paste). After 3 h, the catalyst was filtered off [hydrogen uptake=250 ml] and the filtrate evaporated to dryness, to give an oil which was evaporated to a foam (0.5 g), m.p. 80°-92°. A portion of the foam (0.3 g) in hot ethyl acetate was added to an equivalent amount of maleic acid in hot ethyl acetate. The mixture was cooled and the solid collected, washed with ethyl acetate and dried in vacuo at 60° for 2 days to give the title compound, m.p. >110° (decomposes).

Workup

  1. filtrationthe catalyst was filtered off [hydrogen uptake=250 ml]
  2. customthe filtrate evaporated to dryness
  3. customto give an oil which
  4. customwas evaporated to a foam (0.5 g), m.p. 80°-92°
  5. additionA portion of the foam (0.3 g) in hot ethyl acetate was added to an equivalent amount of maleic acid in hot ethyl acetate
  6. temperatureThe mixture was cooled
  7. customthe solid collected
  8. washwashed with ethyl acetate
  9. customdried in vacuo at 60° for 2 days

Sources & evidence

ORD record
ord-29bb42542eb146fa89df7da1716b9e15
Source dataset
uspto-grants-1989_05
Patent number
US04833153

Reaction notes

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