Ethanolamine → N-(2-Hydroxyethyl)-4-nitrobenzamide

HRID 1648731Notes

Reaction equation

HRID 1648731 reaction equation
C(CN)O.[OH-].[Na+].[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O.[N+:19]([C:22]1[CH:44]=[CH:43][C:25]([C:26]([N:28](C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:29][CH2:30][OH:31])=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>>[N+:19]([C:22]1[CH:44]=[CH:43][C:25]([C:26]([NH:28][CH2:29][CH2:30][OH:31])=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

5

Reactant 4

HCID 700EthanolamineHCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium Hydroxide2×HCID 20481651HCID 20481651, compound

Product 1

HCID 241548N-(2-Hydroxyethyl)-4-nitrobenzamide

Procedure

A solution of 10 ml. ethanolamine in 120 ml. 10% aqueous sodium hydroxide solution was cooled to 5° C. and 30 g. finely powdered 4-nitrobenzoyl chloride added thereto portionwise. The reaction mixture was stirred for 24 hours and filtered. The solid obtained, which mainly consisted of bis-(4-nitrobenzoyl)-ethanolamine, was hydrolysed with 200 ml. of 4% aqueous ethanolic sodium hydroxide at ambient temperature for 24 hours. The reaction mixture was added to the above filtrate, acidified and the precipitated 4-nitrobenzoic acid was filtered off. The filtrate was concentrated and the 13 g. of precipitated N-4-nitrobenzoylethanolamine isolated. The mother liquor was distilled to dryness and the residue was boiled with ethanol. Concentration of the ethanolic extract gave a further 5.3 g. of product; m.p. 134°-135° C.

Workup

  1. filtrationfiltered
  2. customThe solid obtained
  3. additionThe reaction mixture was added to the above filtrate
  4. filtrationthe precipitated 4-nitrobenzoic acid was filtered off
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9fc15128a893440eb226715c8ea38f9d
Source dataset
uspto-grants-1983_11
Patent number
US04412992

Reaction notes

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