Quinoline → HCID 53723341, compound

HRID 1604104Notes

Reaction equation

HRID 1604104 reaction equation
[OH:1][CH2:2][CH:3]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[C:13]([N+:25]([O-])=O)[C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)[CH3:4].N1C2C(=CC=CC=2)C=CC=1>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:25][C:13]1[C:14](=[O:24])[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:12]=1[CH2:11][CH2:10][C@@H:9]1[C@@H:19]2[CH2:20][CH2:21][C@@:22]2([CH3:23])[C@H:8]1[CH2:7][CH2:6][C@@H:5]2[CH:3]([CH2:2][OH:1])[CH3:4]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 54157668HCID 54157668, compound

Product 1

HCID 53723341HCID 53723341, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 20-hydroxymethyl-4-nitropregn-4-en-3-one (2.01 g, 5.35 mM) in absolute ethanol (28 mL) is treated sequentially with Lindlar's catalyst (5% Pd on CaCO3 with 5.2% Pb, 0.81 g) and with quinoline (37 μl) and kept under hydrogen at between 40-55 p.s.i. for 24 hours. The mixture is then filtered through celite, and the filtrate is concentrated to a yellow solid which is purified by short path chromatography to give 4-amino-20-hydroxymethylpregn-4-en-3-one, m.p. 180-185° C. (aqueous isopropanol).

Workup

  1. filtrationThe mixture is then filtered through celite
  2. concentrationthe filtrate is concentrated to a yellow solid which
  3. customis purified by short path chromatography

Sources & evidence

ORD record
ord-69338dcc99c74a07b2a77045da24a447
Source dataset
uspto-grants-1999_11
Patent number
US05990328

Reaction notes

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