Ethyl Acetate → HCID 90415237, compound

HRID 1776705Notes

Reaction equation

HRID 1776705 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[OH-].[Na+].Cl.Cl[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.CCOC(C)=O>C(#N)C>[N+:8]([C:7]1[CH:6]=[CH:5][C:4]([O:11][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)=[CH:3][C:2]=1[NH2:1])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 1675273-Amino-4-nitrophenolHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 90415237HCID 90415237, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-amino-4-nitrophenol (5.0 g, 32 mmol) in acetonitrile (162 mL) was added 4N NaOH (16.2 mL, 4 N) followed by 2-(chloromethyl)quinoline hydrochloride (7.6 g, 34 mmol) and the resulting mixture was stirred at RT for 2 h. The reaction was then heated to 80° C. for 4 h. The reaction mixture was cooled to RT and concentrated to dryness. Water was added to the residue to give a dark orange solid that was isolated by filtration. Trituration using EtOAc then afforded the title compound. MS (ESI): mass calcd. for C16H13N3O3, 295.10; m/z found, 296.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) 8.42 (d, J=8.5, 1H), 8.02 (dd, J=10.0, 9.2, 2H), 7.83-7.75 (m, 1H), 7.68 (d, J=8.5, 1H), 7.66-7.60 (m, 1H), 7.55 (d, J=3.0, 1H), 7.32 (dd, J=9.2, 3.0, 1H), 7.28 (s, 2H), 7.03 (d, J=9.3, 1H), 5.34 (s, 2H).

Workup

  1. temperatureThe reaction was then heated to 80° C. for 4 h
  2. temperatureThe reaction mixture was cooled to RT
  3. concentrationconcentrated to dryness
  4. additionWater was added to the residue
  5. customto give a dark orange solid
  6. customthat was isolated by filtration

Sources & evidence

ORD record
ord-abd705a6611f492bb13b338eb2f42685
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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