Acetic Anhydride → HCID 69184344, compound

HRID 1187430Notes

Reaction equation

HRID 1187430 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68536167HCID 68536167, compound

Product 1

HCID 69184344HCID 69184344, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-{2-[(3-nitroquinolin4-yl)ammo]ethoxy}ethanol (55.5 g, 0.2 mol), acetic anhydride (37.6 mL, 0.4 mol), and pyridine (250 mL) was heated at reflux for 30 minutes. The solution was allowed to cool to ambient temperature and was concentrated under reduced pressure to remove about 50-75% of the pyridine. The residual solution was poured into water to precipitate the product as an oil which solidified upon stirring. The solid was isolated by filtration, washed with water, and dried. The crude product was recrystallized from 2-propanol (200 mL) to provide 55.6 g of 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethyl acetate as a bright yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. concentrationwas concentrated under reduced pressure
  4. customto remove about 50-75% of the pyridine
  5. additionThe residual solution was poured into water
  6. customto precipitate the product as an oil which
  7. customThe solid was isolated by filtration
  8. washwashed with water
  9. customdried
  10. customThe crude product was recrystallized from 2-propanol (200 mL)

Sources & evidence

ORD record
ord-aad5b7fc93f8475fa3db3f65e69ad7a8
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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