Isopropylamine → Ethyl 3-(1-(isopropylamino)phthalazin-6-yl)-4-methylbenzoate

HRID 2357535Notes

Reaction equation

HRID 2357535 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[CH:24]([NH2:27])([CH3:26])[CH3:25]>C(#N)C.ClCCl>[CH:24]([NH:27][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 59726010Ethyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate

Product 1

HCID 68453005Ethyl 3-(1-(isopropylamino)phthalazin-6-yl)-4-methylbenzoate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

Ethyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate (1.4 g) in acetonitrile (10 mL) was treated with isopropylamine (8 mL, 89 mmol). The mixture was stirred at 140° C. (sealed tube) for 15 h. The mixture was dissolved in 100 mL dichloromethane and was washed with water (20 mL), brine (20 mL), then dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 50% ethyl acetate/DCM to give ethyl 3-(1-(isopropylamino)phthalazin-6-yl)-4-methylbenzoate as a white solid.

Workup

  1. custom(sealed tube) for 15 h
  2. washwas washed with water (20 mL), brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography
  6. washeluting with 50% ethyl acetate/DCM

Sources & evidence

ORD record
ord-3accc830932047a398da127755058c10
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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