4-Ethoxyaniline → HCID 22741963, compound

HRID 1057708Notes

Reaction equation

HRID 1057708 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

Procedure

A mixture of 0.3 g (1.173 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine (for preparation see German Auslegeschrft 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. customfor preparation
  2. customThe cooled reaction mixture
  3. washThe organic phase washed with water and brine
  4. dry with materialis dried over anhydrous sodium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-75fd6ae473d5407aa41d023b1f91cd5d
Source dataset
uspto-grants-2003_02
Patent number
US06514974B2

Reaction notes

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