4-(Trifluoromethyl)benzaldehyde → HCID 15524197, compound

HRID 1530845Notes

Reaction equation

HRID 1530845 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.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=1.C([BH3-])#N.[Na+]>CO.O>[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]([CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:27])[F:28])=[CH:24][CH:23]=1)[CH2:8]2

Participants

5

Reactant 3

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21253084HCID 21253084, compound

Product 1

HCID 15524197HCID 15524197, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of the product from Example 5 (1 g, 3.24 mmol) and α,α,α-trifluro-p-tolualdehyde (1.22 g, 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 2.5 hours. The precipitate was filtered, washed with hexane and dried to give the title compound (0.71 g, 51% yield) as a yellow solid, mp=119-120° C.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with hexane
  3. customdried

Sources & evidence

ORD record
ord-1be6fbfd449b424b839623ea5c67a9b4
Source dataset
uspto-grants-2001_03
Patent number
US06197771B1

Reaction notes

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