HCID 19700990, compound → HCID 19700994, compound

HRID 861907Notes

Reaction equation

HRID 861907 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]4[O:23][CH2:22][O:21][C:18]=4[CH:19]=3)[CH:14]([CH3:24])[N:13]([C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[N:12]=2)=[CH:7][CH:6]=1)(=O)C>[OH-].[Na+].CO.CCOC(C)=O.O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]4[O:23][CH2:22][O:21][C:18]=4[CH:19]=3)[CH:14]([CH3:24])[N:13]([C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[N:12]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 1

HCID 19700990HCID 19700990, compound

Product 1

HCID 19700994HCID 19700994, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-(4-acetylaminophenyl)-1,2-dihydro-2-(N,N-dimethylcarbamoyl)-1-methyl-6,7-methylendioxyphthalazine (97 mg, 0.25 mmole) in 1N sodium hydroxide (3 mL) and methanol (7 mL) was heated to reflux for 72 hours, cooled to ambient temperature, diluted with EtOAc (25 mL) and water (25 mL). The aqueous layer was washed with EtOAc and the combined organic layers were dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 25% hexanes/EtOAc to leave a light yellow foamy solid (63 mg, 72%). 200 MHz 1H NMR (CDCl3); δ7.45 (d, 2H, J=8.6 Hz, ArH2 '), 6.84 (s, 1H, ArH), 6.76 (d, 2H, J=8.6 Hz, ArH), 6.71 (s, 1H, ArH), 6.01 (d, 2H, J=2.9 Hz, OCH2O), 5.25 (q, 1H, J=7.1 Hz, CHCH3), 3.95 (brs, 2H, NH2), 3.07 (s, 6H, N(CH3)2), 1.33 (d, 3H, J=7.1 Hz, CHCH3): FTIR (PTFE film); 3456 cm-1, 3343, 3220, 1631, 1605, 1482, 1379, 1251, 1036.

Workup

  1. temperatureto reflux for 72 hours
  2. washThe aqueous layer was washed with EtOAc
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel with 25% hexanes/EtOAc

Sources & evidence

ORD record
ord-2eacc77d4d1744e89d2fcc8e5e783371
Source dataset
uspto-grants-1998_02
Patent number
US05716956

Reaction notes

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