Sodium borohydride → HCID 68001651, compound

HRID 1427414Notes

Reaction equation

HRID 1427414 reaction equation
[NH2:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][N:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[NH2:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86687800HCID 86687800, compound

Product 1

HCID 68001651HCID 68001651, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of the aldehyde obtained above (850 mg, 5.1 mmol) in MeOH (25 mL) at 0° C. was added sodium tetrahydroborate (190 mg, 5.10 mmol) and the reaction mixture warmed to RT for 2 hr and then quenched by the addition of hydrochloric acid (1 M, 5.0 mL) The mixture was diluted with sat aq. NaHCO3 (40 mL) and was extracted with DCM (80 mL, 6×100 mL). The combined organic extracts were dried and evaporated in vacuo to afford (2-amino-3-nitropyridin-4-yl)methanol as an orange solid (630 mg, 69%); Rt 0.40 min (Method 2); m/z 170 (M+H)+, (ES+).

Workup

  1. customquenched by the addition of hydrochloric acid (1 M, 5.0 mL) The mixture
  2. additionwas diluted with sat aq. NaHCO3 (40 mL)
  3. extractionwas extracted with DCM (80 mL, 6×100 mL)
  4. customThe combined organic extracts were dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1cfc0b70379a4fbeb6329d131a861329
Source dataset
uspto-grants-2015_01
Patent number
US08933228B2

Reaction notes

Loading…