Acetic Acid → HCID 21072009, compound

HRID 1372496Notes

Reaction equation

HRID 1372496 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=O)[C:9]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:15][CH2:16][C:17](=[O:19])[CH3:18])[CH2:8]2)(=[O:3])[CH3:2].N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.CCOC(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11]([C:10]3[C:9]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:8]2)[CH2:15][CH2:16][C:17](=[O:19])[CH:18]=3)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 21072001HCID 21072001, compound

Product 1

HCID 21072009HCID 21072009, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5-(acetylamino)-2-butyl-2-(3-oxobutyl)-1-indanone (9.8 g, 31.1 mmol) in toluene (300 mL) was treated with pyrrolidine (2.6 mL, 31 mmol) and acetic acid (1.8 mL, 31 mmol). The mixture was stirred under a N2 atmosphere and heated in an oil bath at 90° C. for two hours. After cooling, the mixture was diluted with EtOAc (500 mL), washed with water, 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to an orange-brown foam (7.0 g). 1H NMR of the crude product showed 7-(acetylamino)-9a-butyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one along with 14–17% of a by-product identified as 9a-butyl-4-methyl-8,9,9a,10-tetrahydro-7H-indeno[1,2-g]quinolin-7-one.

Workup

  1. temperatureAfter cooling
  2. washwashed with water, 5% NaHCO3, water, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum to an orange-brown foam (7.0 g)

Sources & evidence

ORD record
ord-f5d69b2025f74c94a3755e7fbc5e0d25
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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