Methanol → 1-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hemifumarate

HRID 49881Notes

Reaction equation

HRID 49881 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:33]=[CH:32][C:13]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[N:17][N:16]=2)=[CH:12][CH:11]=1.CO>>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[N:17][N:16]=2)=[CH:32][CH:33]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[N:17][N:16]=2)=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 151194VatalanibHCID 444972Fumaric Acid

Product 1

HCID 1317227641-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hemifumarate

Procedure

A solution of 0.696 g (6 mmol) fumaric acid in 20 ml methanol is added to a hot solution of 1.04 g (3 mmol) 1-(4-chloroanilino)-4-(4-pyridylmethyl)phthalazine in 30 ml methanol. As it cools to 0° C., crystals precipitate out; these are filtered off and recrystallized again from methanol. Title compound is obtained after drying under HV (8 h at 100° C.); m.p. 202° C. (decomp.); ESI-MS: (M+H)+=347.

Workup

  1. customcools to 0° C.
  2. customcrystals precipitate out
  3. filtrationthese are filtered off
  4. customrecrystallized again from methanol

Sources & evidence

ORD record
ord-720217273ec24baaa27d2dcf3d6b9ebf
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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