Ethanol ethylacetate → HCID 87788430, compound

HRID 895935Notes

Reaction equation

HRID 895935 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:21][CH3:22])[CH:13]=[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]3=2)[CH:10]=[C:9]1[CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([C:28]1[N:29](CC2C=CC=CC=2)C2C(C=1)=C(OC)C=C1C=CC=CC=21)(=[O:27])C.[C:50]([O:53][CH2:54]C)(=[O:52])C.C([OH:58])C>[Pd].C(Cl)(Cl)Cl>[OH2:21].[CH3:54][O:53][C:50](=[O:52])[CH2:22][O:21][C:12]1[CH:13]=[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]2=[C:16]2[C:11]=1[C:10]([C:25](=[O:27])[C:28]([NH2:29])=[O:58])=[C:9]([CH2:23][CH3:24])[N:8]2[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH2:29][C:28](=[O:58])[C:25]([C:10]1[C:11]2[C:16](=[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]3=[CH:13][C:12]=2[O:21][CH2:22][C:50]([O:53][CH3:54])=[O:52])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]=1[CH2:23][CH3:24])=[O:27]

Participants

6

Reactant 3

HCID 21584252Ethanol ethylacetateHCID 22381001HCID 22381001, compoundHCID 22381010HCID 22381010, compound

Product 1

HCID 87788430HCID 87788430, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

Preparation of 1-benzyl-2-ethyl-4-methoxybenz[g]indole. A mixture of 2-acetyl-1-benzyl-4-methoxybenz[g]indole (0.70 g, 2.1 mmol) and 10% palladium-on-carbon (300 mg) in 1:1 ethyl acetate/ethanol (50 mL) was hydrogenated at room temperature under 40 psi pressure for 18 h. Chloroform (3 mL) was added and the mixture further hydrogenated for 18 h. The mixture was filtered through Celite™ which was washed thoroughly with ethyl acetate. The combined washings were concentrated in vacuo to provide 0.47 g (70%) of the title compound as an off-white solid. 1H NMR (CDCl3) δ7.95 (d, J=8 Hz, 1H), 7.79 (d, J=8 Hz, 1H), 7.25 (m, 4H), 7.15 (t, J=7 Hz, 1H), 7.05 (d, J=8 Hz, 2H), 6.82 (s, 1H), 6.67 (s, 1H), 5.78 (s, 2H), 4.08 (s, 3H), 2.76 (q, J=7 Hz, 2H), 1.37 (t, J=7 Hz, 3H); MS ES+ m/e 315 (p+1); IR (CHCl3, cm−1) 3008, 1531, 1470.

Workup

  1. waitthe mixture further hydrogenated for 18 h
  2. filtrationThe mixture was filtered through Celite™ which
  3. washwas washed thoroughly with ethyl acetate
  4. concentrationThe combined washings were concentrated in vacuo

Sources & evidence

ORD record
ord-f951de5a32f546419fad414a89d28f7e
Source dataset
uspto-grants-2005_07
Patent number
US06916840B2

Reaction notes

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