4,4'-Diazenediyldianiline → N-Boc-pyrrolidine

HRID 71819

Reaction equation

HRID 71819 reaction equation
NC1C=CC(N=NC2C=CC(N)=CC=2)=CC=1.[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH:25]1C(O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(OC(N1C2C(=CC=CC=2)C=CC1)=O)C>C(Cl)Cl>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 108554,4'-DiazenediyldianilineHCID 278131(2H)-Quinolinecarboxylic acid, ethyl esterHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 643455N-Boc-pyrrolidineYield 166.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-aminophenylazo)-phenylamine (3.02 g) and pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (7.00 g) were dissolved in DCM (90 mL), and 1-ethoxycarbonyl-1,2-dihydroquinoline (8.45 g) was added. The reaction mixture was stirred at ambient temperature for 19 hours and evaporated under vacuum. Oil was dissolved in ethyl acetate, forming a precipitate, which was collected by vacuum filtration and dried under vacuum, giving 2-(4-{4-[(1-carboxylic acid tert-butyl ester-pyrrolidine-2-carbonyl)-amino]-phenylazo}-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (9.28 g) as a brown solid.

Workup

  1. customevaporated under vacuum
  2. dissolutionOil was dissolved in ethyl acetate
  3. customforming a precipitate, which
  4. filtrationwas collected by vacuum filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-004b028f6ee8484e9f6058adb3c2a4da
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Linked notes

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