Acetaldehyde → HCID 86632907, compound

HRID 1628549Notes

Reaction equation

HRID 1628549 reaction equation
[F:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:13](O[BH3-])(=O)[CH3:14].[Na+].CO.[CH:21](=O)[CH3:22]>C(=O)([O-])O.[Na+].[OH-].[Na+].C(O)(=O)C>[CH2:21]([N:8]([CH2:13][CH3:14])[C:5]1[C:4]([NH2:9])=[C:3]([N+:10]([O-:12])=[O:11])[C:2]([F:1])=[CH:7][CH:6]=1)[CH3:22]

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 887MethanolHCID 103521351,2-Benzenediamine, 4-fluoro-3-nitro-HCID 23670382Sodiumacetoxyborohydride

Product 1

HCID 86632907HCID 86632907, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 4-fluoro-3-nitrobenzene-1,2-diamine (800 mg, 4.67 mmol), sodium acetoxyborohydride (5.94 g, 28.0 mmol), methanol (9 mL) and acetic acid (2.3 mL) was added acetoaldehyde (90%, 1.75 mL, 28.1 mmol) at 0° C. After the resultant mixture was stirred at 0° C. for 30 min, the mixture was diluted with aqueous sodium hydrogen carbonate and aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10 ethyl acetate/n-hexane mixture to give the title compound as a red oil (942 mg, 4.15 mmol, 89%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 10 ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-c295f82ed6664145b3b6797362c0798e
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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