Acetic Acid → HCID 22451913, compound

HRID 365640Notes

Reaction equation

HRID 365640 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-2a5a855e28e54dbcadb5c973e8af51cc
Source dataset
uspto-grants-2000_10
Patent number
US06127359

Reaction notes

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