Reaction equation
[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[C@H:5]1[CH2:20][C:9]2=[CH:10][NH:11][C:12]3=[CH:13][CH:14]=[C:15]([C:16]([NH:18][NH2:19])=[O:17])[C:7](=[C:8]23)[CH2:6]1)[CH2:2][CH3:3]>COC(OC)(OC)C1C=CC=CC=1.C(Cl)Cl>[C:7]1([C:15]2[O:17][C:16]([C:15]3[CH:14]=[CH:13][C:12]4[NH:11][CH:10]=[C:9]5[CH2:20][C@H:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:21][CH2:22][CH3:23])[CH2:6][C:7]=3[C:8]=45)=[N:18][N:19]=2)[CH:8]=[CH:9][CH:20]=[CH:5][CH:6]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 0.20 g (0.64 mmol) of (4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6-carboxylic hydrazide in 2.0 ml of trimethylorthobenzoate was heated at 135° C. under nitrogen for 5 hours. After cooling, the semisolid mixture was dissolved in methylene chloride and the product was extracted into aqueous tartaric acid. The aqueous solution was basified with sodium carbonate and the product was extracted into methylene chloride. Evaporation of the methylene chloride left crystalline product which was then chromatographed over 3 g of silica gel using ethyl acetate as eluent. The product from the column was recrystallized from toluene to give 0.21 g of title compound.
Workup
- temperatureAfter cooling
- extractionthe product was extracted into aqueous tartaric acid
- extractionthe product was extracted into methylene chloride
- customEvaporation of the methylene chloride
- waitleft crystalline product which
- customwas then chromatographed over 3 g of silica gel
- customThe product from the column was recrystallized from toluene
Sources & evidence
- ORD record
- ord-caa328d5a9ed459587c9da23d001ab2e
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05624944
Linked notes
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