N-Methylisatoic anhydride → 3-(o-Methylaminobenzoyl)-3,4-dihydro-phthalazin-1(2H)-one

HRID 364220Notes

Reaction equation

HRID 364220 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3][NH:2]1.[CH3:12][N:13]1C(=O)O[C:16](=[O:17])[C:15]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:14]12>C1(C)C(C)=CC=CC=1>[CH3:12][NH:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[C:16]([N:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:11])[NH:2]1)=[O:17]

Participants

4

Reactant 2

HCID 25160N-Methylisatoic anhydrideHCID 122144653,4-Dihydrophthalazin-1(2H)-one

Product 1

HCID 136703963-(o-Methylaminobenzoyl)-3,4-dihydro-phthalazin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
25 °C

Procedure

To 3.3 g (0.022 ml) of 3,4-dihydro-phthalazin-1(2H)-one dissolved in 100 ml of xylene was added 3.9 g (0.022 mol) of N-methylisatoic anhydride and the solution was stirred and heated at reflux under N2 for 16 hours. The mixture was then cooled to room temperature (about 25° C.) whereupon a heavy precipitate formed. The 3-(o-methylaminobenzoyl)-3,4-dihydro-phthalazin-1(2H)-one was collected as a solid, washed well with xylene to give an off-white powder, mp 199°-202° C.

Workup

  1. temperatureheated
  2. temperatureat reflux under N2 for 16 hours
  3. customformed
  4. customThe 3-(o-methylaminobenzoyl)-3,4-dihydro-phthalazin-1(2H)-one was collected as a solid
  5. washwashed well with xylene
  6. customto give an off-white powder, mp 199°-202° C.

Sources & evidence

ORD record
ord-8ad631097f3b4a8aba5c90f5a003f8b9
Source dataset
uspto-grants-1986_08
Patent number
US04604464

Reaction notes

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