Hydrochloric Acid → HCID 86654061, compound

HRID 1948109Notes

Reaction equation

HRID 1948109 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][N:10]1[C:19]2[C:14](=[C:15]([N+:20]([O-])=O)[CH:16]=[CH:17][CH:18]=2)[C:13](=[O:23])[C:12]([CH3:24])=[CH:11]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[ClH:25].[H][H]>CO.CCOCC.[Pd]>[ClH:25].[CH2:1]([O:3][P:4]([CH2:9][N:10]1[C:19]2[C:14](=[C:15]([NH2:20])[CH:16]=[CH:17][CH:18]=2)[C:13](=[O:23])[C:12]([CH3:24])=[CH:11]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 86654063HCID 86654063, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86654061HCID 86654061, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (3-Methyl-5-nitro-4-oxo-4H-quinolin-1-ylmethyl)-phosphonic acid diethyl ester (Compound 303B, 20 mg; 0.05 mmol) in methanol (5 mL) was charged with Pd/C (5 mg) and 1M HCl in ether (1 mL) under nitrogen and stirred under 1 atmosphere of hydrogen overnight at RT. The solution was filtered the filtrate concentrated to get the final compound (yield 20 mg; 99%; tlc 1:9 MeOH:DCM); 1H NMR (300 MHz, CDCl3), δ ppm, 8.12 (s, 1H), 8.01 (d, 6 Hz, 1H,) 7.88-7.83 (m, 1H) 7.40 (d, J=9 Hz, 1H) 4.12-4.13 (m, 4H,) 3.31-3.29 (m, 2H), 2.14 (s, 3H), 1.27-1.25 (m, 6H)

Workup

  1. filtrationThe solution was filtered the filtrate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6687054231894633b2367823325d4ad3
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

Loading…