Trifluoroacetic acid → 7-(4-Fluoro-benzyl)-9-hydroxy-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853618Notes

Reaction equation

HRID 853618 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21]COC)=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:25][CH3:26])[C:9]=3[C:8]2=[O:27])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:25][CH3:26])[C:9]=3[C:8]2=[O:27])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589288257-(4-Fluoro-benzyl)-5-methoxy-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione

Product 1

HCID 104506377-(4-Fluoro-benzyl)-9-hydroxy-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude diether 8 (0.0223 g, 0.0527 mmol) was dissolved in 1 mL dichloromethane. Ten equivalents of trifluoroacetic acid was added. The mixture was stirred at room temperature for 45 minutes. The reaction mixture was concentrated and azeotroped with toluene (2×) to give crude 7-(4-fluoro-benzyl)-9-hydroxy-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione 9 which was triturated with 8 mL of 1:1 diethylether/hexane and filtered to give 9 (0.0161 g, 0.0456 mmol, 83% for two steps). 1H NMR (CDCl3) δ 9.0 (br s, 1 H), 8.7 (d, 1 H), 7.7 (d, 1H), 7.5 (m, 2 H), 7.0 (t, 2 H), 4.8 (s, 2H), 4.4 (s, 3H). (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped with toluene (2×)

Sources & evidence

ORD record
ord-6263fedf24824c6cbcd20c8e99cc42f2
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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