Sulfuric Acid → 5-(p-Aminophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 2290578Notes

Reaction equation

HRID 2290578 reaction equation
C([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(O)=O.S(=O)(=O)(O)O.[NH:24]=[N+]=[N-]>C(Cl)CCl>[NH2:24][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24530Hydrazoic acidHCID 136882154-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)benzoic acid

Product 1

HCID 152947205-(p-Aminophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2.42 g of 5-p-carboxyphenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 100 ml of ethylene dichloride is treated with 6 ml of concentrated sulfuric acid. The reaction mixture is heated to 40° and 6 ml of hydrazoic acid (2M in ethylene dichloride) is added dropwise. When gas evolution has ceased, the reaction is evaporated. The residue is redissolved in water and adjusted to pH 10. The aqueous phase is extracted with methylene chloride (3×30 ml). The organic extracts are dried over potassium carbonate and evaporated to yield the title compound (a).

Workup

  1. temperatureThe reaction mixture is heated to 40°
  2. customthe reaction is evaporated
  3. dissolutionThe residue is redissolved in water
  4. extractionThe aqueous phase is extracted with methylene chloride (3×30 ml)
  5. dry with materialThe organic extracts are dried over potassium carbonate
  6. customevaporated

Sources & evidence

ORD record
ord-c5cfb8290fed460a8075e7c7e8d51e6e
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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