Butylamine → HCID 19699634, compound

HRID 862892Notes

Reaction equation

HRID 862892 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:8]3=[CH:7][C:6]=2[C:5](Cl)=[N:4][N:3]=1.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22]>>[CH2:19]([NH:23][C:2]1[C:11]2[CH:10]=[C:9]3[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:8]3=[CH:7][C:6]=2[C:5]([NH:3][CH2:2][CH2:11][CH2:6][CH3:5])=[N:4][N:3]=1)[CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 19699636HCID 19699636, compound

Product 1

HCID 19699634HCID 19699634, compoundYield 48%

Procedure

A mixture of 1,4-dichloro-6-methoxybenzo[g]phthalazine (3.94 mmol) and n-butylamine (25 mL) was treated in an autoclave at 130° C. for 6 h. After cooling to room temperature, the excess n-butylamine was evaporated to dryness under vacuum and the residue was extracted with chloroform (2×50 mL). The resulting extracts were concentrated and purified by flash chromatography on silica gel 60 Merck (200-400 mesh), using a mixture of chloroform, benzene, methanol (v/v, 1:0.5:0.2) as eluent. The removal of the solvents from the fraction of Rf=0.11 afforded 0.67 g (48%) of 1,4-bis(n-butylamino)-6-methoxy-benzo[g]phthalazine as a brown solid, melting at 178°-180° C., which shows the following physical properties:

Workup

  1. additionwas treated in an autoclave at 130° C. for 6 h
  2. customthe excess n-butylamine was evaporated to dryness under vacuum
  3. extractionthe residue was extracted with chloroform (2×50 mL)
  4. concentrationThe resulting extracts were concentrated
  5. custompurified by flash chromatography on silica gel 60 Merck (200-400 mesh)
  6. additiona mixture of chloroform, benzene, methanol (v/v, 1:0.5:0.2) as eluent
  7. customThe removal of the solvents from the fraction of Rf=0.11

Sources & evidence

ORD record
ord-e266af48a129454fb971ee368936a502
Source dataset
uspto-grants-1998_02
Patent number
US05719282

Reaction notes

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