Ethanol → HCID 19816098, compound

HRID 2247861Notes

Reaction equation

HRID 2247861 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)([O-])=O.C([OH:22])C>O=[Pt]=O>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N+:10]1([O-:22])[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 702EthanolHCID 198160942-(4-Nitropyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 19816098HCID 19816098, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

To a slurry of PtO2 (0.3 g) in 10 ml of ethanolwas added 2-(4-nitro-3-pyridinyl)-1,2,3,4-tetrahydroisoquinoline, N-oxide (5.0 g) in 240 ml of ethanol and this was hydrogenated with a Parr apparatus at room temperature for 24 hours. The mixture was filtered and the filtrate concentrated to yield an oil (5.1 g), which was eluted with 20% methanol/DCM on a silica gel column via HPLC. The desired fractions were concentrated to a solid (2.0 g), m.p. 216°-219° C. (decomp). This solid was recrystallized from acetonitrile to yield a solid, 1.0 g, m.p. 217°-219° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f5cfdaf0e8134d20bc4e187d0ce9a61f
Source dataset
uspto-grants-1991_08
Patent number
US05037835

Reaction notes

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