Pyrrolidine → HCID 15613919, compound

HRID 2351531Notes

Reaction equation

HRID 2351531 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[OH:13])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[N+:14]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23](=O)[CH3:24])=[CH:19][CH:18]=1)([O-:16])=[O:15].N1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:24][C:23]1([CH2:22][O:21][C:20]2[CH:26]=[CH:27][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=2)[CH2:2][C:1](=[O:3])[C:4]2[C:12](=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=2)[O:13]1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 3085071-(4-Nitrophenoxy)propan-2-oneHCID 521998p-Toluenesulfonic acid monohydrateHCID 91792453-Acetyl-4-hydroxybenzoic acid

Product 1

HCID 15613919HCID 15613919, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A procedure similar to that described in Preparation 1 was repeated, except that 10 g of 3-acetyl-4-hydroxybenzoic acid, 13 g of 4-nitrophenoxyacetone, 7.9 g of pyrrolidine, 2.6 g of p-toluenesulfonic acid monohydrate and 150 ml of benzene were reacted, to afford 17.6 g of the title compound as pale brown crystals, melting at 227°-235° C.

Workup

  1. customA procedure similar to that described in Preparation 1
  2. customwere reacted

Sources & evidence

ORD record
ord-34429053a693483fb9427a74a74b96e0
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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