Dimethylformamide → HCID 57162619, compound

HRID 1018362Notes

Reaction equation

HRID 1018362 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O)([O-])=O.[C:14]([O:18][C:19](=[O:22])[CH2:20]Br)([CH3:17])([CH3:16])[CH3:15].CN(C=[O:27])C>>[C:14]([O:18][C:19](=[O:22])[CH:20]([OH:27])[CH2:9][C:8]1[CH:11]=[CH:12][CH:13]=[C:6]([NH2:3])[CH:7]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 74493-NitrobenzaldehydeHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 57162619HCID 57162619, compoundYield 41%

Conditions

Temperature
65 °C

Procedure

Sodium hydride (60% dispersion in oil) (1.32 g, 33.0 mmol) was added to a solution of 3-nitro-benzaldehyde (4.53 g, 30.0 mmol) and tert-butyl-bromoacetate (4.87 ml, 33.0 mmol) in DMF (100 ml). The resulting suspension was heated at 65° C. for 2 h, cooled, then quenched with water (10 ml). The mixture was diluted with ethyl acetate (100 ml), the organic phase was washed with water (150 ml), brine (2×150 ml), dried (MgSO4) and the solvent was evaporated. The residue was dissolved in dioxan (50 ml) and hydrogenated over palladium on charcoal (10%, 1.00 g) for 24 h. The catalyst was removed by filtration and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, hexane/ethyl acetate 1:1) to afford colourless oil (2.95 g, 41%). 1H NMR (300 MHz, CDCl3) 7.07 (1H, m), 6.60 (3H, m), 4.30 (1H, dd), 3.61 (2H, br s), 3.00 (1H, dd), 2.85 (2H, m), 1.46 (9H, s).

Workup

  1. temperaturecooled
  2. customquenched with water (10 ml)
  3. additionThe mixture was diluted with ethyl acetate (100 ml)
  4. washthe organic phase was washed with water (150 ml), brine (2×150 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in dioxan (50 ml) and hydrogenated over palladium on charcoal (10%, 1.00 g) for 24 h
  8. customThe catalyst was removed by filtration
  9. customthe solvent was evaporated
  10. customThe crude product was purified by flash column chromatography (silica, hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-afdae29de750448d9d4b18b7da8515fe
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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