3-Chloroaniline → HCID 51356955, compound

HRID 1623748Notes

Reaction equation

HRID 1623748 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl:31][C:32]1[CH:33]=[C:34]([NH2:38])[CH:35]=[CH:36][CH:37]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([Cl:31])[CH:33]=1)=[O:9]

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 51356955HCID 51356955, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method B; 200 mg, 0.65 mmol) was added to a stirred suspension of CDI (106 mg, 0.65 mmol) in THF (6 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min. 3-Chlorobenzenamine (83 mg, 0.65 mmol) was then added dropwise. After refluxing for 14 h, the reaction mixture was concentrated to obtain crude product. The crude product was purified by silica gel chromatography eluting with hexane:ethyl acetate (10:1) to yield the title compound. 110 mg.

Workup

  1. temperatureAfter refluxing for 14 h
  2. concentrationthe reaction mixture was concentrated
  3. customto obtain crude product
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate (10:1)

Sources & evidence

ORD record
ord-73af5b3be55041258c729afaa0bfbc7d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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