Hydrochloric Acid → HCID 13669789, compound

HRID 2290837Notes

Reaction equation

HRID 2290837 reaction equation
Cl.[O:2]([CH2:9][CH2:10][O:11][C:12]([C:14]1[CH:23]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[C:26]([CH3:31])[C:25]=2[Cl:32])[C:22]2[C:21](=[O:33])[CH2:20][N:19](CC3C=CC=CC=3)[CH2:18][C:17]=2[NH:16][C:15]=1[CH3:41])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.O.[H][H]>[Pd].CO>[O:2]([CH2:9][CH2:10][O:11][C:12]([C:14]1[CH:23]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[C:26]([CH3:31])[C:25]=2[Cl:32])[C:22]2[C:21](=[O:33])[CH2:20][NH:19][CH2:18][C:17]=2[NH:16][C:15]=1[CH3:41])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 13669752HCID 13669752, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13669789HCID 13669789, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Twelve grams of the above hydrochloride, 125 ml of methanol, 2 ml of concentrated hydrochloric acid, 10 ml of water, and 1 g of 10% palladium on carbon were shaken with hydrogen (50 psig initial pressure) for 24 hours. The mixture was diluted with 500 ml of methanol, heated to reflux and filtered. The filtrate was evaporated to dryness and the residue was slurried with ethanol and filtered. The solid was recrystallized from methanol to obtain 5.2 g of the title compound as the hydrochloride, m.p. 252°-5° C. dec.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. filtrationfiltered
  6. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-cd88fb3c70044115831e0042f2a835d2
Source dataset
uspto-grants-1986_10
Patent number
US04618678

Reaction notes

Loading…