Sulfuric Acid → 2-nitro-6,7-dihydro [5H] benzocycloheptene-7-methanamine

HRID 1764723Notes

Reaction equation

HRID 1764723 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]2[CH2:8][CH2:9][CH:10]([CH2:14][NH2:15])[CH2:11][CH:12](O)[C:6]=2[CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O>O1CCOCC1>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]2[CH2:8][CH2:9][CH:10]([CH2:14][NH2:15])[CH:11]=[CH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 543770273-nitro-7-aminomethyl-6,7,8,9-tetrahydro [5H] benzocycloheptene-5-ol

Product 1

HCID 539809212-nitro-6,7-dihydro [5H] benzocycloheptene-7-methanamineYield 108.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 10 g of the product of Step D in 100 ml of dioxane under nitrogen was heated to reflux and 20 ml of concentrated sulfuric acid were added thereto dropwise over 3 minutes. The mixture was stirred at reflux for 20 minutes and was then concentrated to 50 ml under reduced pressure. 300 ml of water were added and the neutral fraction was removed with ether. The aqueous phase was made alkaline at 10° C. with sodium hydroxide and was then extracted with methylene chloride. The organic extracts were dried and evaporated to dryness to obtain 10 g of 2-nitro-6,7-dihydro [5H] benzocycloheptene-7-methanamine in the form of a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureat reflux for 20 minutes
  4. concentrationwas then concentrated to 50 ml under reduced pressure
  5. addition300 ml of water were added
  6. customthe neutral fraction was removed with ether
  7. customat 10° C.
  8. extractionwas then extracted with methylene chloride
  9. customThe organic extracts were dried
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-aef9f80435ef474b8ba24b0e6ac26690
Source dataset
uspto-grants-1978_09
Patent number
US04117164

Reaction notes

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