Ammonium Acetate → HCID 13672384, compound

HRID 542551Notes

Reaction equation

HRID 542551 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-:19])=[C:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:38].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-:19])=[C:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:38])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 13672382HCID 13672382, compound

Product 1

HCID 13672384HCID 13672384, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 5 m moles of 4-benzyloxy-2-(10-formyldecyl) quinoline-N-oxide is dissolved in methanol, and 50 m moles of ammonium acetate and 15 m moles of sodium cyanoborohydride are added thereto with ice cooling. Then, the mixture is stirred for 1.5 hours. After the reaction, the solvent is removed therefrom by distillation, and then the mixture is extracted with chloroform. The chloroform layer is dried over anhydrous sodium sulfate, and the solvent is removed therefrom by distillation. The residue is purified by silica gel column procedure, whereby the captioned compound is obtained as colorless crystals (yield: 21.5%).

Workup

  1. customAfter the reaction
  2. customthe solvent is removed
  3. distillationby distillation
  4. extractionthe mixture is extracted with chloroform
  5. dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
  6. customthe solvent is removed
  7. distillationby distillation
  8. customThe residue is purified by silica gel column procedure, whereby the captioned compound

Sources & evidence

ORD record
ord-702747bdab064f4aa7858051f3318234
Source dataset
uspto-grants-1987_04
Patent number
US04657916

Reaction notes

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