Hydrochloric Acid → Hydrochloric Acid

HRID 513650Notes

Reaction equation

HRID 513650 reaction equation
[N+:1]([C:4]1[C:5]([CH2:14][NH:15]S(C(C)(C)C)=O)=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[ClH:22].O1CCOCC1>CO>[N+:1]([C:4]1[C:5]([CH2:14][NH2:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[ClH:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 866697652-Methyl-propane-2-sulfinic acid (8-nitro-quinolin-7-ylmethyl)-amide2×

Product 2

HCID 313Hydrochloric AcidYield 100%HCID 68183319C-(8-Nitro-quinolin-7-yl)-methylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-methyl-propane-2-sulfinic acid (8-nitro-quinolin-7-ylmethyl)-amide (Intermediate 209) (402 mg, 1.31 mmol) in dry MeOH (10 ml) under a nitrogen atmosphere was cooled to 0° C. HCl in dioxane (4M, 1.7 ml, 6.9 mmol) was added and the mixture was stirred at 0° C. for 1 h and allowed to warm to room temperature overnight. The mixture was concentrated in vacuo and the residue was triturated with dry ether (10 ml). The solid was collected by filtration, washed with dry ether and dried at room temperature to give the title compound as an HCl salt (180 mg, 100%).

Workup

  1. temperatureto warm to room temperature overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was triturated with dry ether (10 ml)
  4. filtrationThe solid was collected by filtration
  5. washwashed with dry ether
  6. customdried at room temperature

Sources & evidence

ORD record
ord-f7752c57c07e446fa182cf464a352fec
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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