Nitric Acid → HCID 13338331, compound

HRID 2417560Notes

Reaction equation

HRID 2417560 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:13])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:13])[CH2:8][CH2:7][C:6]=2[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 123981Benalfocin

Product 1

HCID 13338331HCID 13338331, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cold solution of 67.2 g (0.34 mol, U.S. Pat. No. 4,265,890) of 6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in 100 ml of sulfuric acid was added, dropwise over 2 hours, 40 ml of concentrated nitric acid. The mixture was stirred at room temperature overnight and quenched in ice. It was made basic with 10% sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed, dried and evaporated to leave a residue, which was chromatographed over a "Waters prep 500" high pressure liquid chromatographic silica gel column, using isopropanol-hexane-diethylamine, to give pure 6-chloro-3-methyl-9-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. customquenched in ice
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed
  4. customdried
  5. customevaporated
  6. customto leave a residue, which
  7. customwas chromatographed over a "Waters prep 500" high pressure liquid chromatographic silica gel column

Sources & evidence

ORD record
ord-31d68f86b1564eabb89d08154a1d4c7a
Source dataset
uspto-grants-1984_09
Patent number
US04469634

Reaction notes

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