Nitric Acid → 8-Chloro-5-nitro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene

HRID 266173Notes

Reaction equation

HRID 266173 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH2:14][CH:13]([NH:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][CH3:26])[CH2:12][CH2:11]2.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O.[N+](C)([O-])=O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([N+:1]([O-:4])=[O:2])=[C:10]2[C:15]=1[CH2:14][CH:13]([NH:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][CH3:26])[CH2:12][CH2:11]2

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 190326628-Chloro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 190326608-Chloro-5-nitro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6375NitromethaneSolvent

Procedure

Fuming nitric acid (100 ml), 33% in concentrated sulphuric acid was added dropwise to a solution of 72g (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).

Workup

  1. customto reach ambient temperature
  2. additionAfter pouring on ice water/diethyl ether the mixture
  3. customthe phases separated
  4. dry with materialThe organic phase was dried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated to a residue of 65.5 g of an isomeric mixture
  7. washElution of the mixture on a silica column (isooctane/diethyl ether, 1:1)

Sources & evidence

ORD record
ord-62ba9f99488542c0ab8588e3ae72da6a
Source dataset
uspto-grants-1997_07
Patent number
US05650427

Reaction notes

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