Water → HCID 178460503, compound

HRID 2048126Notes

Reaction equation

HRID 2048126 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[C:11]([CH3:23])=[C:12]([C:21]#[N:22])[C:13](=[O:20])[N:14]([CH2:17][CH2:18][OH:19])[C:15]=2[OH:16])=[C:4]([N+:24]([O-:26])=[O:25])[CH:3]=1.N1C=C[CH:30]=[CH:29][CH:28]=1.[OH2:33]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[C:11]([CH3:23])=[C:12]([C:21]#[N:22])[C:13](=[O:20])[N:14]([CH2:17][CH2:18][O:19][C:28](=[O:33])[CH:29]=[CH2:30])[C:15]=2[OH:16])=[C:4]([N+:24]([O-:26])=[O:25])[CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 1049PyridineHCID 178430932HCID 178430932, compound

Product 1

HCID 178460503HCID 178460503, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methacryloyl anhydride (17.9 g, 0.116 mol) is added to a stirred mixture of 5-(4-chloro-2-nitrophenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methylpyrid-2-one (22 g, 058 mol) and pyridine (25 ml) in methylene chloride (200 ml). The mixture is stirred under reflux for 24 hours, forming a solution after ca. 5 hr. After cooling to 20° C. water (20 ml) is added, with stirring, followed by more water (200 ml) after a further 2 hours. The organic layer is collected and the solvent removed to leave a tarry residue which is stirred at 70° C. for 20 minutes, with aqueous methylated spirits. The resulting brownish yellow solid is collected (21.3 g, 82%). This crude product is passed through silica gel using (methylene chloride:hexane 80:20) as eluant. The solvent is removed and the residue is crystallised from methylene chloride/isopropanol.

Workup

  1. temperatureunder reflux for 24 hours
  2. customforming a solution after ca. 5 hr
  3. additionis added
  4. stirringwith stirring
  5. customThe organic layer is collected
  6. customthe solvent removed
  7. customto leave a tarry residue which
  8. customThe resulting brownish yellow solid is collected (21.3 g, 82%)
  9. customThe solvent is removed
  10. customthe residue is crystallised from methylene chloride/isopropanol

Sources & evidence

ORD record
ord-55031de08b6e44cdb6728be58b2a5ecd
Source dataset
uspto-grants-2013_11
Patent number
US08593719B2

Reaction notes

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