Ammonium Chloride → 9-Benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide

HRID 51439Notes

Reaction equation

[Cl-].[NH4+:2].C[Al](C)C.[CH2:7]([N:14]1[C:26]2[CH2:25][CH2:24][CH2:23][CH:22]([C:27](OCC)=[O:28])[C:21]=2[C:20]2[C:15]1=[C:16]([CH3:34])[CH:17]=[CH:18][C:19]=2[O:32][CH3:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.ClCCl>[CH2:7]([N:14]1[C:26]2[CH2:25][CH2:24][CH2:23][CH:22]([C:27]([NH2:2])=[O:28])[C:21]=2[C:20]2[C:15]1=[C:16]([CH3:34])[CH:17]=[CH:18][C:19]=2[O:32][CH3:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A slurry of 0.38 g of ammonium chloride in 15 ml of dry toluene was cooled in an ice bath and treated with 3.5 ml of a 2.0 M solution of trimethylaluminum in toluene. This mixture was stirred for 1 hour at room temperature, whereupon 0.762 g (2.02 mmol) of ethyl 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylate in 10 ml of toluene and 1 ml of dichloromethane was added. The mixture was heated to 50° C. overnight, cooled and quenched with 20 ml of aqueous 5% HCl solution. Ethyl acetate extracts (3×100 ml) were washed with water and then with brine, dried over magnesium sulfate and concentrated to afford 0.693 g (98%) of the subtitle compound. ESIMS m/e 349 (M++1) NMR (300 MHz, CDCl3): δ7.25 (m, 3H); 6.83 (d, J=7.2, 2H); 6.74 (d, J=7.8, 1H); 6.40 (d, J=7.8, 1H); 5.93 (br, 1H); 5.54 and 5.45 (ABq, J=17.7, 2H); 5.42 (br, 1H); 4.14 (br, 1H); 3.87 (s, 3H); 2.65 (dt, J=16.4, 4.1, 1H); 2.55-2.36 (m,2H); 2.45 (s, 3H); 1.97-1.86 (m, 3H).

Workup

additionwas added
temperaturecooled
customquenched with 20 ml of aqueous 5% HCl solution
washwere washed with water
dry with materialwith brine, dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-7be7a1cc5e5944caa306fa2ef8eb0564
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713645B1

Reaction notes

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