HCID 20385078, compound → 3-Sulphamoyl-4-phenoxy-5-[gamma-(1-pyrrolyl)-propyl]-benzoic acid

HRID 47096Notes

Reaction equation

HRID 47096 reaction equation
[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH2:21][CH2:22][C:23]#[N:24])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([OH:10])=[O:9])(=[O:4])(=[O:3])[NH2:2]>CO.N.[Ni]>[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH2:21][CH2:22][CH2:23][N:24]2[CH:12]=[CH:13][CH:5]=[CH:6]2)[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([OH:10])=[O:9])(=[O:3])(=[O:4])[NH2:2]

Participants

5

Reactant 1

HCID 20385078HCID 20385078, compound

Product 1

HCID 130210803-Sulphamoyl-4-phenoxy-5-[gamma-(1-pyrrolyl)-propyl]-benzoic acid

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

The nitrile (3.46 g) is dissolved in 70 ml of methanol saturated with ammonia, the solution is after-saturated for 30 minutes under an ammonia pressure of 5 bars and, after adding 1 g of Raney Ni, is hydrogenated for 12 hours at 70°-80° C. and under an initial hydrogen pressure of 100 bars. The catalyst is then filtered off and washed with methanol and the filtrate is evaporated. After taking up the residue in a little water, the solution is acidified and extracted by shaking with ethyl acetate and the acid aqueous phase is again evaporated, dried and extracted with ethanol, the ethanol extract is concentrated to 30 ml and ether is added: 3-sulphamoyl-4-phenoxy-5-[γ-aminopropyl]-benzoic acid hydrochloride crystallises out; melting point 259°-262° C.

Workup

  1. waitis hydrogenated for 12 hours at 70°-80° C. and under an initial hydrogen
  2. filtrationThe catalyst is then filtered off
  3. washwashed with methanol
  4. customthe filtrate is evaporated
  5. extractionextracted
  6. customthe acid aqueous phase is again evaporated
  7. customdried
  8. extractionextracted with ethanol
  9. extractionthe ethanol extract
  10. concentrationis concentrated to 30 ml and ether
  11. additionis added
  12. custom3-sulphamoyl-4-phenoxy-5-[γ-aminopropyl]-benzoic acid hydrochloride crystallises out

Sources & evidence

ORD record
ord-509fd6c3ea764fbf8d6e777495f6b00c
Source dataset
uspto-grants-1979_11
Patent number
US04176190

Reaction notes

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