Acetic Acid → HCID 23291001, compound

HRID 365637Notes

Reaction equation

HRID 365637 reaction equation
[Cl: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([BH3-])#N.[Na+].C(O)(=O)C>CO>[Cl: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 AcidHCID 1001PhenethylamineHCID 729332-Chloro-5-nitrobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23291001HCID 23291001, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-5-nitro-benzaldehyde (5 g, 27 mmol) and 2-phenylethylamine (4.1 g, 33.75 mmol) were dissolved in methanol, cooled to 0° C., and sodium cyanoborohydride (2.1 g, 33.75 mmol) was added. The reaction was adjusted to pH 6 with acetic acid and warmed to room temperature for 6 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 methylene chloride. The organic extracts were washed with water and brine and dried briefly over sodium sulfate. Filtration of the mixture and concentration of the filtrate in vacua yielded the title compound (82%).

Workup

  1. temperaturewarmed to room temperature for 6 h
  2. customThe reaction mixture was quenched with ice
  3. additiondiluted with water
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe organic extracts were washed with water and brine
  6. dry with materialdried briefly over sodium sulfate
  7. filtrationFiltration of the mixture and concentration of the filtrate in vacua

Sources & evidence

ORD record
ord-b81fbd3513c14e329971e623760e2a46
Source dataset
uspto-grants-2000_10
Patent number
US06127359

Reaction notes

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