HCID 19700992, compound → HCID 19700985, compound

HRID 861906Notes

Reaction equation

HRID 861906 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]([CH2:24][CH3:25])[N:13]([C:26](=[O:29])[NH:27][CH3:28])[N:12]=2)=[CH:7][CH:6]=1)(=O)C>[OH-].[Na+].CO.CCOC(C)=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]([CH2:24][CH3:25])[N:13]([C:26](=[O:29])[NH:27][CH3:28])[N:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 19700992HCID 19700992, compound

Product 1

HCID 19700985HCID 19700985, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-(4-acetylaminophenyl)-1,2-dihydro-1-ethyl-2-methylcarbamoyl-6,7-methylendioxyphthalazine (45 mg, 0.11 mmole) in 1N sodium hydroxide (4 mL) and methanol (6 mL) was heated to reflux for 72 hours. The mixture was cooled to ambient temperature, diluted with EtOAc (30 mL), washed with water (25 mL), dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel with 25% hexanes/EtOAc to afford the product as a light yellow foamy solid (35 mg, 90%). 200 MHz 1H NMR (CDCl3); δ7.42 (d, 2H, J=8.1 Hz, ArH), 6.82 (s, 1H, ArH), 6.76 (d, 2H, J=8.1 Hz, ArH), 6.70 (s, 1H, ArH), 6.50 (brq, 1H, J=5.4 Hz, NHCH3), 5.59 (d, 2H, J=2.7 Hz, OCH2O), 5.48 (t, 1H, J=6.8 Hz, CHCH2), 2.93 (d, 3H, J=5.4 Hz, NHCH3), 1.64 (m, 2H, CHCH2 CH3), 0.87 (t, 3H, J=8.1 Hz, CH2CH3).

Workup

  1. temperatureto reflux for 72 hours
  2. washwashed with water (25 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel with 25% hexanes/EtOAc

Sources & evidence

ORD record
ord-e6515ce5b7cc4d95aa8772255f29f752
Source dataset
uspto-grants-1998_02
Patent number
US05716956

Reaction notes

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