Acetic Acid → HCID 22672522, compound

HRID 47965Notes

Reaction equation

HRID 47965 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:28][CH2:29][CH2:30][OH:31])[CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:15][CH:14]=1.[OH-].[K+].C(O)(=O)C>C1COCC1.O.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[N:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]([CH2:28][CH2:29][CH2:30][OH:31])[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 22672523Ethyl 4-((4-((2-chloro-4-nitrophenyl)diazenyl)phenyl)(3-hydroxypropyl)amino)butanoate

Product 1

HCID 22672522HCID 22672522, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

To a stirred solution of 20 (4.48 g, 10 mmole) in 40 mL of THF added 40 mL of ethanol followed by a solution of KOH (0.84 g, 15 mmol) in 20 mL of water and 20 mL of ethanol. The mixture is stirred overnight and concentrated. The residue suspended in 125 mL of water, treated with 2.6 mL (˜3 eqv.) of acetic acid, and cooled to 4° C. The resulting solid is filtered off, washed with water, and dried. Yield is quantitative. 1H NMR (DMSO-d6) δ: 8.42 (d, J=2.5 Hz, aromatic proton, 1H), 8.23 (dd, J1=9 Hz, J2=2.5 Hz, aromatic proton, 1H), 7.82 (d, J=9 Hz, 2H), 7.90 (d, J=9 Hz, 1H), 7.03 (d, J=9 Hz, aromatic protons, 2H), 4.8 (br s, OH, 1H), 3.5 (m, aliphatic protons, 6H), 1.86 (t, J=6 Hz, aliphatic protons, 2H), 1.72 (m, aliphatic protons, 4H).

Workup

  1. concentrationconcentrated
  2. filtrationThe resulting solid is filtered off
  3. washwashed with water
  4. customdried
  5. customYield

Sources & evidence

ORD record
ord-d071368eb9a34efaae1e551807003c1b
Source dataset
uspto-grants-2004_03
Patent number
US06699975B2

Reaction notes

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