Water → HCID 12795109, compound

HRID 648005Notes

Reaction equation

HRID 648005 reaction equation
[OH-:1].[K+].[C:3]([CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]2[CH:12]=[CH:13][CH:14]=[C:6]12)#N.[OH2:15]>C(O)CO>[CH:14]1[CH:13]=[CH:12][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:5]([C:3]([OH:15])=[O:1])[C:6]=12

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 12795081HCID 12795081, compound

Product 1

HCID 12795109HCID 12795109, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of potassium hydroxide (2.02 g) in water (1.2 ml.) is added to a solution of 9-cyano-5,6,7,8-tetrahydro-9H-pyrrolo[1,2-a]azepine (1.0 g., 0.006 moles) in ethylene glycol (11 ml.) at 5°. The solution thus obtained is placed in an oil bath at 118° and after 3 hours the cooled solution is poured into water (50 ml.). The aqueous alkaline phase is extracted with ether (20 ml.) the aqueous phase is made acidic to pH-2 with concentrated hydrochloric acid at 5°. The product is extracted into ethyl acetate (4×40 ml.), the extract is washed with water to neutrality, dried and evaporated. Crystallization of the residue from ethyl acetate-ether gave 5,6,7,8-tetrahydro-9H-pyrrolo[1,2,a]azepine-9-carboxylic acid, (92% yield), m.p. 129°-130° C.

Workup

  1. customThe solution thus obtained
  2. extractionThe aqueous alkaline phase is extracted with ether (20 ml.) the aqueous phase
  3. customis made acidic to pH-2 with concentrated hydrochloric acid at 5°
  4. extractionThe product is extracted into ethyl acetate (4×40 ml.)
  5. washthe extract is washed with water to neutrality
  6. customdried
  7. customevaporated
  8. customCrystallization of the residue from ethyl acetate-ether

Sources & evidence

ORD record
ord-f44eeb5fe5ca4e10bf3c31d832618c05
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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