methyl (4-amino-2,3-dihydro-1H-indol-3-yl)acetate → 1,2,2a,5-Tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

HRID 74574

Reaction equation

HRID 74574 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([CH2:11][C:12]([O:14]C)=O)[CH2:5][NH:6]2>C1(C)C(C)=CC=CC=1>[NH:6]1[C:7]2[C:3]3[CH:4]([CH2:11][C:12](=[O:14])[NH:1][C:2]=3[CH:10]=[CH:9][CH:8]=2)[CH2:5]1

Participants

3

Reactant 1

HCID 10104433methyl (4-amino-2,3-dihydro-1H-indol-3-yl)acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.80 g (8.73 mmol) methyl (4-amino-2,3-dihydro-1H-indol-3-yl)acetate in 100 mL xylene were refluxed for 30 h. The reaction mixture was evaporated down and purified by flash chromatography. The product-containing fractions were combined and evaporated down.

Workup

  1. customThe reaction mixture was evaporated down
  2. custompurified by flash chromatography
  3. customevaporated down

Sources & evidence

ORD record
ord-cdbb45a4f8dd41cead89feda40477465
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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