Benzaldehyde → HCID 15524188, compound

HRID 1106424Notes

Reaction equation

HRID 1106424 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO.O.C([BH3-])#N.[Na+]>ClCCl>[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:8]2

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21253084HCID 21253084, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 15524188HCID 15524188, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 5 (1 g, 3.24 mmol) and benzaldehyde (0.71 mL, 7 mmol) in 2:1 MeOH/H2O (50 mL) was treated with sodium cyanoborohydride (0.56 g, 9 mmol) portionwise under nitrogen and stirred for six hours. The reaction mixture was then added to dichloromethane (150 mL) and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and activated charcoal, filtered through a plug of silica gel and concentrated under vacuum to dryness. The solids were triturated in hexane, filtered, and oven dried to give the title compound (0.73 g, 62% yield) as an orange solid, mp=150-152° C.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over magnesium sulfate and activated charcoal
  3. filtrationfiltered through a plug of silica gel
  4. concentrationconcentrated under vacuum to dryness
  5. customThe solids were triturated in hexane
  6. filtrationfiltered
  7. customoven dried

Sources & evidence

ORD record
ord-f93e578a7cf54e1da69895f8eaeda361
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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