Sodium borohydride → Methyl 1-methyl-8-nitro-1,2-dihydroquinoline-7-carboxylate

HRID 925619Notes

Reaction equation

HRID 925619 reaction equation
FC(F)(F)S([O-])(=O)=O.[CH3:9][O:10][C:11]([C:13]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[N+:20]2[CH3:26])=[CH:15][CH:14]=1)=[O:12].[BH4-].[Na+]>CO>[CH3:26][N:20]1[C:21]2[C:16](=[CH:15][CH:14]=[C:13]([C:11]([O:10][CH3:9])=[O:12])[C:22]=2[N+:23]([O-:25])=[O:24])[CH:17]=[CH:18][CH2:19]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 891885797-(Methoxycarbonyl)-1-methyl-8-nitroquinolinium trifluoromethanesulfonate

Product 1

HCID 71014122Methyl 1-methyl-8-nitro-1,2-dihydroquinoline-7-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-(methoxycarbonyl)-1-methyl-8-nitroquinolinium trifluoromethanesulfonate (2.10 g, 5.30 mmol) in MeOH (27 mL) at 0° C. was added NaBH4 (200 mg, 5.30 mmol). The mixture was stirred at rt for 1 h. The resulting solution was quenched with saturated aqueous NH4Cl and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated to afford methyl 1-methyl-8-nitro-1,2-dihydroquinoline-7-carboxylate in pure form.

Workup

  1. customThe resulting solution was quenched with saturated aqueous NH4Cl
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9fc36636d27424fa42b3b5bf69e11a8
Source dataset
uspto-grants-2016_03
Patent number
US09284312B2

Reaction notes

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