HCID 131715711, compound → HCID 22839553, compound

HRID 622078Notes

Reaction equation

HRID 622078 reaction equation
[ClH:1].[F:2][C:3]1[C:22]2[O:21][C@H:10]3[CH2:11][N:12](CC4C=CC=CC=4)[CH2:13][C@@H:9]3[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>CO.[Pd]>[ClH:1].[F:2][C:3]1[C:22]2[O:21][C@H:10]3[CH2:11][NH:12][CH2:13][C@@H:9]3[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 131715711HCID 131715711, compound

Product 1

HCID 22839553HCID 22839553, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 3 (1.2 g) in methanol (50 mls) was hydrogenated over 10% palladium on charcoal (0.2 g) for 17 hours. The catalyst was filtered off, and the filtrate was evaporated to dryness. Crystallisation of the resulting solid from isopropyl alcohol/methanol gave the title compound (0.63 g). M.p. 259°. NMR (DMSOd6) δ 9.9 (2H, Br S, NH2+), 7.2-6.85 (3H, m, aromatic), 4.24 (1H, d of t, 3a-H), 3.8-2.78 (6H, m, 1-H2, 3-H2, 9-H2), 2.27 (1H, m, 9a-H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customCrystallisation of the resulting solid from isopropyl alcohol/methanol

Sources & evidence

ORD record
ord-c7ce4ddc96fa44bdafefebe2fdcbd013
Source dataset
uspto-grants-1988_09
Patent number
US04769367

Reaction notes

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