Sodium borohydride → 2-Methyl-propane-2-sulfinic acid (8-nitro-quinolin-7-ylmethyl)-amide

HRID 513649Notes

Reaction equation

HRID 513649 reaction equation
[N+:1]([C:4]1[C:5](/[CH:14]=[N:15]/[S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[C:5]([CH2:14][NH:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 88861906(NE)-2-methyl-N-[(8-nitroquinolin-7-yl)methylidene]propane-2-sulfinamide2×

Product 1

HCID 866697652-Methyl-propane-2-sulfinic acid (8-nitro-quinolin-7-ylmethyl)-amideYield 102.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methyl-propane-2-sulfinic acid 1-(8-nitro-quinolin-7-yl)-meth-(E)-ylideneamide (Intermediate 208) (400 mg, 1.3 mmol) in MeOH (8 ml) under a nitrogen atmosphere was cooled to 0° C. Sodium borohydride (1.24 g, 3.3 mmol) was added and the mixture was allowed to warm to room temperature while stirring for 16 h. The reaction mixture was concentrated in vacuo and the residue was diluted with sat. sodium bicarbonate solution (15 ml), extracted with EtOAc followed by 10% MeOH/DCM. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (411 mg, 100%). The material was used in the next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with sat. sodium bicarbonate solution (15 ml)
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebc556ccd60143038d0494e18571a433
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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