Chlorobenzene → HCID 22752789, compound

HRID 2163524Notes

Reaction equation

HRID 2163524 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:16])[N:4]([CH2:17][CH2:18]Br)[N:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][NH:32][CH3:33])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(=O)([O-])[O-].[Na+].[Na+].[Cl:40]C1C=CC=CC=1>>[ClH:40].[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:16])[N:4]([CH2:17][CH2:18][N:32]([CH3:33])[CH2:31][CH2:30][C:24]2[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=2)[N:3]=1

Participants

5

Reactant 4

HCID 7964ChlorobenzeneHCID 10340Sodium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 133270312-(2-Bromoethyl)-6,7-dimethoxy-4-methyl-1(2H)-phthalazinone

Product 1

HCID 22752789HCID 22752789, compound

Procedure

A solution of 2.5 gm (7.6 millimols) of 1-[4-methyl-6,7-dimethoxy-1(2H)-phthalazinone-2-yl]-2-bromo-ethane in 50 ml of chlorobenzene was admixed with 1.5 gm (7.6 millimols) of 3,4-dimethoxyphenylethyl-N-methylamine and 3.0 gm of sodium carbonate, and the mixture was refluxed for 20 hours. After cooling, the precipitated solid was filtered off, and the filtrate was evaporated. The residue was chromatographed on silica gel (chloroform/methanol = 100/1), the main fractions were evaporated and the base was precipitated as its hydrochloride, yielding 1.8 gm (49% of theory) of the compound of the formula ##STR13## which had a melting point of 204-205° C.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated solid was filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was chromatographed on silica gel (chloroform/methanol = 100/1)
  6. customthe main fractions were evaporated
  7. customthe base was precipitated as its hydrochloride
  8. customyielding 1.8 gm (49% of theory) of the compound of the formula ##STR13## which

Sources & evidence

ORD record
ord-bef8fbf28afb413685eaab9765dc6ed7
Source dataset
uspto-grants-1979_01
Patent number
US04134980

Reaction notes

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