Hydrochloric Acid → HCID 13669802, compound

HRID 1982580Notes

Reaction equation

HRID 1982580 reaction equation
Cl.[Cl:2][C:3]1[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:4]=1[O:5][CH2:6][CH2:7][O:8][C:9]([C:11]1[CH:20]([C:21]2[C:26]([F:27])=[C:25]([F:28])[C:24]([F:29])=[C:23]([F:30])[C:22]=2[F:31])[C:19]2[C:18](=[O:32])[CH2:17][N:16](CC3C=CC=CC=3)[CH2:15][C:14]=2[NH:13][C:12]=1[CH3:40])=[O:10].CO.Cl.[H][H]>[Pd].O>[Cl:2][C:3]1[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:4]=1[O:5][CH2:6][CH2:7][O:8][C:9]([C:11]1[CH:20]([C:21]2[C:22]([F:31])=[C:23]([F:30])[C:24]([F:29])=[C:25]([F:28])[C:26]=2[F:27])[C:19]2[C:18](=[O:32])[CH2:17][NH:16][CH2:15][C:14]=2[NH:13][C:12]=1[CH3:40])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13669765HCID 13669765, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13669802HCID 13669802, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

The hydrochloride from above (10 g), 500 ml of methanol, 25 ml of water, 5 ml of concentrated hydrochloric acid and 0.5 g of 10% palladium on carbon were shaken with hydrogen (45 psig initial pressure) for 4 hours. The catalyst was separated and the solution was evaporated to dryness. The residue was dissolved in ethyl acetate and shaken with dilute sodium hydroxide solution. The ethyl acetate solution was dried over magnesium sulfate, then evaporated to dryness. The residue was dissolved in methanol and saturated with hydrogen chloride. The solution was evaporated to dryness. The residue crystallized on standing with ethyl acetate for 3 days. The solid was treated with boiling ethyl acetate and filtered to obtain the title compound as the hydrochloride, m.p. 228°-231° C. dec.

Workup

  1. customThe catalyst was separated
  2. customthe solution was evaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in methanol and saturated with hydrogen chloride
  7. customThe solution was evaporated to dryness
  8. customThe residue crystallized
  9. additionThe solid was treated with boiling ethyl acetate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-deff91871cf3451083c39a6367f75cab
Source dataset
uspto-grants-1986_06
Patent number
US04596873

Reaction notes

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