3-Nitrobenzaldehyde → HCID 19375041, compound

HRID 128792Notes

Reaction equation

HRID 128792 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8].[N+](C1C=C(C=CC=1)C=O)([O-])=O.C(N(CC)CC)C.[C:32](Cl)(=[O:40])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>ClCCl>[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][C:5]1[CH:6]=[C:7]([NH:8][C:32](=[O:40])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 19375083HCID 19375083, compound

Product 1

HCID 19375041HCID 19375041, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the method outlined in example 9 above, 3-(2,2-dimethoxyethyl)aniline is prepared from 3-nitrobenzaldehyde. To a solution of this material (2.13 g) in dichloromethane (25 ml) is added triethylamine (1.7 ml). The solution is cooled in an ice bath, and octanoyl chloride (2.0 ml) is added dropwise with stirring. After 10 min, the solvent is removed in vacuo and the residue is taken up in ether, filtered, and washed with aqueous sodium bicarbonate. The solution is dried, filtered, and concentrated to leave N-(3-(2,2-dimethoxyethyl)phenyl)octanamide (3.4 g) as a light brown oil. By the method of example 2 above, this is converted into the title compound, mp 128°-130° after recrystallization from dichloromethane.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. customthe solvent is removed in vacuo
  3. filtrationfiltered
  4. washwashed with aqueous sodium bicarbonate
  5. customThe solution is dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8195c36abf8d4402af7d800309f923e5
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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