Hydrochloric Acid → HCID 13669787, compound

HRID 2290834Notes

Reaction equation

HRID 2290834 reaction equation
Cl.[O:2]([CH2:9][CH2:10][O:11][C:12]([C:14]1[CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[C:22]2[C:21](=[O:31])[CH2:20][N:19](CC3C=CC=CC=3)[CH2:18][C:17]=2[NH:16][C:15]=1[CH3:39])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.Cl.[H][H]>[Pd].O>[O:2]([CH2:9][CH2:10][O:11][C:12]([C:14]1[CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[C:22]2[C:21](=[O:31])[CH2:20][NH:19][CH2:18][C:17]=2[NH:16][C:15]=1[CH3:39])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13669745HCID 13669745, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13669787HCID 13669787, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

The hydrochloride from above (21.5 g), 500 ml of methanol, 5 ml of concentrated hydrochloric acid, 15 ml of water and 0.6 g of 10% palladium on carbon were shaken with hydrogen (50 psig initial pressure) for 20 hours. The catalyst was separated and the solution was evaporated to dryness in vacuo. The residue was slurried with diethyl ether and filtered. The solid was triturated with refluxing ethanol, filtered and dried to obtain 12 g of the title compound as the hydrochloride, m.p. 238°-240° C. dec.

Workup

  1. customThe catalyst was separated
  2. customthe solution was evaporated to dryness in vacuo
  3. filtrationfiltered
  4. customThe solid was triturated with refluxing ethanol
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-e5ab4cbdd04a4ebdb530597d456794bd
Source dataset
uspto-grants-1986_10
Patent number
US04618678

Reaction notes

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