Hydrochloric Acid → HCID 70383008, compound

HRID 622079Notes

Reaction equation

HRID 622079 reaction equation
C1(C[N:8]2[CH2:12][C@@H:11]3[CH2:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[O:16][C@H:10]3[CH2:9]2)C=CC=CC=1.[ClH:21].[H][H]>CO.[Pd]>[ClH:21].[CH2:12]1[NH:8][CH2:9][C@@H:10]2[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH2:13][C@@H:11]12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22839550HCID 22839550, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70383008HCID 70383008, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To the compound of Example 5 (1.09 g) in methanol (40 ml) was added 10.9M hydrogen chloride in methanol (0.41 ml) and 10% palladium on charcoal (0.1 g). The mixture was hydrogenated at 50° until hydrogen uptake ceased. The catalyst was removed by filtration and the filtrate evaporated to give a white solid. Recrystallisation from propan-1-ol gave the title compound (0.56 g) m.p. darkens from 225° and melts 265°-270° (d), NMR (DMSO-d6) τ 2.7-3.2 (4H, multiplets, aromatic), 5.85 (1H, m, 3a-H), 6.2-6.5 and 6.8-7.3 (6H, multiplets, 1-H2, 3-H2 and 9-H2), and 7.77 (1H, m, 9a-H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customto give a white solid
  4. customRecrystallisation from propan-1-ol

Sources & evidence

ORD record
ord-1a7bb4c922854d7fbe0a9bb3928f7674
Source dataset
uspto-grants-1988_09
Patent number
US04769367

Reaction notes

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