Pyridine → HCID 20336031, compound

HRID 1706472Notes

Reaction equation

HRID 1706472 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.N1C=CC=CC=1.[CH2:23]([O:27][C:28]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:29]=1[C:30](Cl)=[O:31])[CH2:24][CH2:25][CH3:26]>O1CCOCC1.CC(C)=O>[CH2:23]([O:27][C:28]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:29]=1[C:30]([NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)=[O:31])[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 1049PyridineHCID 128632402-Butoxy-5-chlorobenzoyl chlorideHCID 20463408Ethyl 4-(2-aminoethyl)-phenylacetate hydrochloride

Product 1

HCID 20336031HCID 20336031, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 12.2 g. ethyl 4-(2-aminoethyl)-phenylacetate hydrochloride in 40 ml dioxane and 40 ml acetone, there is added dropwise, after the addition of 8 ml pyridine, a solution of 12.3 g 2-butoxy-5-chlorobenzoyl chloride in 10 ml acetone. The reaction mixture is then stirred under reflux for 3 hours and thereafter evaporated in a vacuum. The residue is stirred with dilute hydrochloric acid and then with aqueous sodium bicarbonate solution, filtered with suction and washed with water. There are obtained 19 g of crude product which, after recrystallization from ethanol, with the addition of small amounts of water, gives ethyl 4-[2-(2-butoxy-5-chlorobenzamido)-ethyl]-phenylacetate; m.p. 80° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customevaporated in a vacuum
  3. stirringThe residue is stirred with dilute hydrochloric acid
  4. filtrationwith aqueous sodium bicarbonate solution, filtered with suction
  5. washwashed with water
  6. customThere are obtained 19 g of crude product which
  7. customafter recrystallization from ethanol
  8. additionwith the addition of small amounts of water

Sources & evidence

ORD record
ord-4eb80917354849b58e3e11607162ae27
Source dataset
uspto-grants-1980_06
Patent number
US04207341

Reaction notes

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