Nitric Acid → HCID 58494611, compound

HRID 516217Notes

Reaction equation

HRID 516217 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[N+:23]([O-:26])([OH:25])=[O:24]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:7][C:6]=2[C:5]([N+:23]([O-:26])=[O:24])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 58494950HCID 58494950, compound

Product 2

HCID 58494611HCID 58494611, compoundHCID 66982620HCID 66982620, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 11.86 g of ethyl 6-chloro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate in 30 ml of chloroform was ice-cooled, and while maintaining the inner temperature at 10° C. or lower, 60 ml of concentrated sulfuric acid was added thereto. Then, 3.2 ml of concentrated nitric acid was added dropwise thereto, followed by stirring for 30 minutes. The reaction mixture was poured into ice, followed by extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 6.442 g of ethyl 6-chloro-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a reddish orange viscous substance and 5.201 g of ethyl 6-chloro-9-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a pale yellow solid.

Workup

  1. temperaturecooled
  2. additionThe reaction mixture was poured into ice
  3. extractionfollowed by extraction with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-a94024b9ebc645f48a1d0540acb934cb
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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