Hydrochloric Acid → 1,2,2a,5-Tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

HRID 551009Notes

Reaction equation

HRID 551009 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:13][C:14]([O:16]CC)=O)[CH2:7][NH:8]2)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl.C([O-])(O)=O.[Na+]>O.CCO>[NH:8]1[C:9]2[C:5]3[CH:6]([CH2:13][C:14](=[O:16])[NH:1][C:4]=3[CH:12]=[CH:11][CH:10]=2)[CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 57457652HCID 57457652, compound

Product 1

HCID 104421921,2,2a,5-Tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl (4-nitro-2,3-dihydro-1H-indol-3-yl)acetate, enantiomer B, from Step B (1.50 g, 5.99 mmol) in H2O (50 mL) and EtOH (42 mL) was added sodium hydrosulfite (ca. 85%; 4.91 g, 24 mmol). The reaction mixture was stirred at ambient temperature for 1 h, then 3 N hydrochloric acid (14 mL, 42 mmol) was added and the solution was heated to 100° C. for 3 h. The cooled mixture was adjusted to pH 8 with saturated aqueous NaHCO3, then extracted with CH2Cl2 (6×200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=175 (M+1).

Workup

  1. temperaturethe solution was heated to 100° C. for 3 h
  2. extractionextracted with CH2Cl2 (6×200 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19884890df714fc6bff3fe930ddf7074
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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