Diisobutylaluminumhydride → N,O-Dimethylhydroxylamine

HRID 2354136Notes

Reaction equation

HRID 2354136 reaction equation
[Br:1][C:2]1[C:3]([C:8]([N:10]([O:12][CH3:13])C)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[C:3]([CH:8]=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][NH:10][O:12][CH3:13]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59380827HCID 59380827, compound

Product 2

HCID 14232N,O-DimethylhydroxylamineHCID 164142313-Bromopyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-N-methoxy-N-methylpyridine-2-carboxamide (3-2; 219 mg, 0.89 mmole) in dry THF (4 mL) was added diisobutylaluminum hydride (0.94 mL, 0.94 mmole, 1M solution in CH2Cl2) slowly at −78° C. After 3 hr the mixture was quenched with 1N HCl and stirred vigorously. After 4 hr the mixture was neutralized with 1M NaOH and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give 3-bromopyridine-2-carboxaldehyde and its animal with N,O-dimethylhydroxylamine as a mixture which was used in the next step without purification.

Workup

  1. customAfter 3 hr the mixture was quenched with 1N HCl
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f0ad0b050cf40c3ab7c18e86eed00b9
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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