Methylamine → HCID 91619139, compound

HRID 708894Notes

Reaction equation

HRID 708894 reaction equation
[F:1][C:2]1[C:3]([OH:13])=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=O.[CH3:14][NH2:15].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:4]([CH2:5][NH:15][CH3:14])[C:3]=1[OH:13]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 152945723-Fluoro-2-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 91619139HCID 91619139, compoundYield 133%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 17C (2.65 g, 14.32 mmol) in MeOH (100 mL), methylamine (33% in EtOH, 1.960 mL, 15.75 mmol) was added dropwise and stirred rt for 1 h. The reaction mixture was cooled to 0° C., sodium borohydride (0.596 g, 15.75 mmol) was added portionwise and the mixture was stirred at rt for 1 h. The reaction was quenched with 0.5 N HCl, extracted with EtOAc (3×20 mL), washed with water, brine, dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography to give 27A (3.8 g, 18.98 mmol, 133% yield) yellow solid. MS (ESI) m/z: 201.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe mixture was stirred at rt for 1 h
  3. customThe reaction was quenched with 0.5 N HCl
  4. extractionextracted with EtOAc (3×20 mL)
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customEtOAc was removed under reduced pressure
  8. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-17b26349038543e89279e5e02702cc56
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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