Water → 9-Benzhydryloxy-7-(2,4-dimethoxy-benzyl)-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853699Notes

Reaction equation

HRID 853699 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(O[C:10](=O)[O:11][C:12]1[C:21]2[C:22](=[O:37])[N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=3[O:35][CH3:36])[C:24](=[O:25])[C:20]=2[C:19]([O:38][CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2)C.O.IC>O1CCCC1.C(OCC)(=O)C>[CH:39]([O:38][C:19]1[C:20]2[C:24](=[O:25])[N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=3[O:35][CH3:36])[C:22](=[O:37])[C:21]=2[C:12]([O:11][CH3:10])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 58928675carbonic acid 9-benzhydryloxy-7-(2,4-dimethoxy-benzyl)-6,8-dioxo-7,8-dihydro-6H-pyrrolo [3,4-g]quinolin-5-yl ester ethyl ester

Product 1

HCID 589290149-Benzhydryloxy-7-(2,4-dimethoxy-benzyl)-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (2.6 g, 19.0 mmol) and N,N-dimethyl-aminopyridine (DMAP, 0.464 g, 3.8 mmol) were added to carbonic acid 9-benzhydryloxy-7-(2,4-dimethoxy-benzyl)-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester ethyl ester 301 (1.2 g, 1.9 mmol) dissolved in tetrahydrofuran (40 ml) and water (20 ml) was added. After stirring overnight at room temperature, the reaction mixture was concentrated in vacuo and diluted with ethyl acetate. It was washed twice with 5% citric Acid (aqueous), twice with water, once with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was dissolved in dimethylformamide (10 ml). To this reaction mixture was added potassium carbonate (1.24 g, 9.0 mmol) and iodomethane (methyl iodide, MeI, 2.55 g, 18.0 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with ethyl acetate, washed twice with 5% citric acid, twice with water, once with brine, and concentrated in vacuo to afford 9-benzhydryloxy-7-(2,4-dimethoxy-benzyl)-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione 302 (1.1 g, 1.9 mmol, 100%). 1H NMR (d-DMSO) δ 9.16 (dd, 1H), 8.60 (dd, 1H), 7.82 (s, 1H), 7.75 (m, 1H), 7.54 (d, 4H), 7.16 (m, 6H), 6.82 (d, 1H), 6.56 (d, 1H), 6.44 (dd, 1H), 4.66 (s, 2H), 4.10 (s, 3H), 3.76 (s, 3H), 3.70 (s, 3H). MS: 583.2 (M+23).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washIt was washed twice with 5% citric Acid (aqueous), twice with water, once with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting residue was dissolved in dimethylformamide (10 ml)
  7. stirringAfter stirring overnight at room temperature
  8. washwashed twice with 5% citric acid, twice with water, once with brine
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c57823a803446cfa812c31b1b310a2c
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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