3-(N-propionyl-N-n-propylamino)chroman → 8-Chloro-7-nitro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene
Reaction equation
[Cl:1][C:2]1[C:3]([N+:24]([O-:26])=[O:25])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10](N)[CH:9](C(=O)C1C=CC=CC=1CCC)[CH2:8][CH2:7]2.C(N([CH:35]1[CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)O[CH2:36]1)CCC)(=O)CC.NC1C=C2C(CCCC2[N:56](CCC)[C:57](=[O:60])CC)=CC=1>>[Cl:1][C:2]1[C:3]([N+:24]([O-:26])=[O:25])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([NH:56][C:57](=[O:60])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:43]=1[CH2:44][CH2:35][CH3:36])[CH2:8][CH2:7]2Participants
Procedure
Fuming nitric acid (100 ml), 33% in concentrated sulphuric acid was added dropwise to a solution of 72 g (0.22 mol) 8-chloro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene in 300 ml nitromethane at 0° C. The mixture was allowed to reach ambient temperature and was stirred over night. After pouring on ice water/diethyl ether the mixture was basified (sodium carbonate solution) and the phases separated. The organic phase was dried (magnesium sulphate), filtered and evaporated to a residue of 65.5 g of an isomeric mixture. Elution of the mixture on a silica column (isooctane/diethyl ether, 1:1) gave 19 g of 8-chloro-5-nitro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene and 12 g of the desired isomer; 8-chloro-7-nitro-2-(n-propylbenzoyl)-amino-1,2,3,4-tetrahydronaphthalene. MS m/e 372 (M+, 3), 374 (M+ +2, isotope, 1), 105 (100), 164 (72), 77 (35), 134 (16), 165 (9).
Sources & evidence
- ORD record
- ord-9a674ac6b9f74c44b078cc2e1117dc26
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05461061
Reaction notes
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