Ethyl Acetate → HCID 21818461, compound

HRID 1894743Notes

Reaction equation

HRID 1894743 reaction equation
[CH:1]1[C:9]2[C:4]3=[C:5]([CH2:10][CH2:11][N:3]3[C:2]=1C(O)=O)[CH:6]=[CH:7][CH:8]=2.C(OCC)(=O)C>N1C2C(=CC=CC=2)C=CC=1.[Cr]([O-])([O-])=O.[Cu+2]>[CH2:1]1[C:9]2[C:4]3=[C:5]([CH:10]=[CH:11][N:3]3[CH2:2]1)[CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 22556762HCID 22556762, compound

Product 1

HCID 21818461HCID 21818461, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 178505374HCID 178505374, compoundCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4,5-dihydro-pyrrolo[3,2,1-hi]indole-2-carboxylic acid (120 mg, 0.64 mmol) and copper chromite (50 mg) in quinoline (5 ml) in a sealed vessel was heated to 200° C. in a microwave for 20 minutes. After cooling to room temperature the mixture was poured into ethyl acetate (100 ml) and washed with 1M hydrochloric acid (3×100 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (SiO2, 20% EtOAc in hexanes) to yield 1,2-dihydro-pyrrolo[3,2,1-hi]indole as a pale yellow crystalline solid (56 mg). 400 MHz 1H NMR (CDCl3) δ: 7.33 (d, J=8.0 Hz, 1H), 7.14 (d, J=2.8 Hz, 1H), 7.04-6.97 (m, 1H), 6.91 (d, J=6.8 Hz, 1H), 6.44 (d, J=2.8 Hz, 1H), 4.51 (t, J=7.2 Hz, 2H), 3.80 (t, J=7.2 Hz, 2H); LCMS: 144 [M+H].

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed with 1M hydrochloric acid (3×100 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by preparative thin layer chromatography (SiO2, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0a0f6547f5ab43faa2d4f6bf0660850b
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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