4-Ethoxyaniline → HCID 22741963, compound

HRID 1384132Notes

Reaction equation

HRID 1384132 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[CH2:19]([O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CO>[CH2:19]([O:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)=[CH:24][CH:23]=1)[CH3:20]

Participants

5

Reactant 3

HCID 90764-EthoxyanilineHCID 10340Sodium CarbonateHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 22741963HCID 22741963, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.3 g (1.173 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine (for preparation see German Auslegeschrift no. 1 061 788 [published 23.07.1959]), and 0.483 g (3.52 mmol) 4-ethoxyaniline is heated for 30 min at 90° C. The cooled reaction mixture is distributed with thorough stirring between a dichloromethane/methanol mixture (18:1) and saturated aqueous sodium carbonate solution. The organic phase washed with water and brine is dried over anhydrous sodium sulfate and evaporated under vacuum. Title compound is obtained after recrystallization of the residue from acetate/methanol and acetonitrile; m.p. 223-224° C.; ESI-MS: (M+H)+=357.

Workup

  1. customThe cooled reaction mixture
  2. washThe organic phase washed with water and brine
  3. dry with materialis dried over anhydrous sodium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-82b73a9373e7481a9a02f5b53b117032
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

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