Acetic Acid → HCID 22451913, compound

HRID 2186049Notes

Reaction equation

HRID 2186049 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[C:13]1([CH2:19][CH2:20][NH2:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][NH:21][CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 1001PhenethylamineHCID 27347702-Fluoro-5-nitrobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22451913HCID 22451913, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Fluoro-5-nitro-benzaldehyde (11.9 g, 70 mmol) and 2-phenylethylamine (13 mL, 0.1 mol) were dissolved in methanol (150 mL) and glacial acetic acid (15 mL). The solution was cooled to 0° C., and sodium cyanoborohydride (6.6 g, 0.1 mol) was added portionwise. The reaction was adjusted to pH 6 with acetic acid and stirred at room temperature for 24 h. The reaction mixture was quenched with ice and diluted with water. The pH was adjusted to 11 with sodium hydroxide and the mixture was extracted with EtOAc. The organic extracts were washed with cold dilute HCl solution and a solid precipitated. Filtration yielded the title compound (15.6 g, 82%). Mp 235-6° C.; MS m/e 275 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with ice
  2. additiondiluted with water
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic extracts were washed with cold dilute HCl solution
  5. customa solid precipitated
  6. filtrationFiltration

Sources & evidence

ORD record
ord-47cbb8d252b54c8f8b383ab014690d5d
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

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