P-Anisidine → 7-Acetamino-1-(4-methoxyanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

HRID 49874Notes

Reaction equation

HRID 49874 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[I-].[Li+].[NH:12]([C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH2:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[N:21][N:22]=[C:23]2[Cl:26])=[CH:18][CH:17]=1)[C:13]([CH3:15])=[O:14]>C(O)CCC>[ClH:26].[NH:12]([C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH2:27][C:28]3[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=3)=[N:21][N:22]=[C:23]2[NH:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:18][CH:17]=1)[C:13]([CH3:15])=[O:14]

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 66321Lithium iodideHCID 227419517-Acetamino-1-chloro-4-(4-pyridylmethyl)phthalazine

Product 1

HCID 227419527-Acetamino-1-(4-methoxyanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Under exclusion of air, 354 mg (2.88 mmol) 4-methoxyaniline and 13 mg lithium iodide are added to 300 mg (0.96 mmol) 7-acetamino-1-chloro-4-(4-pyridylmethyl)phthalazine in 3.9 ml 1-butanol and heated to boiling for 20 h. After cooling, the dark suspension is filtered off, washed with 1-butanol and ethanol, and dried to obtain title compound: m.p.: 160-163° C.; HPLC: tRet(Grad5-40)=9.5; FAB MS (M+H)+=400.

Workup

  1. temperatureheated
  2. temperatureAfter cooling
  3. filtrationthe dark suspension is filtered off
  4. washwashed with 1-butanol and ethanol
  5. customdried

Sources & evidence

ORD record
ord-eecac6dc705c4f16956787ade5bf30d5
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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