4-Chloroaniline → HCID 15086593, compound

HRID 359081Notes

Reaction equation

HRID 359081 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]([CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)=O.C(B)#N.[Na]>CO>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:9][CH2:11][O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 11636984methyl 4-formylmethyloxybenzoateHCID 101953985CID 101953985

Product 1

HCID 15086593HCID 15086593, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Chloroaniline (0.99 g) and methyl 4-formylmethoxybenzoate (1.5 g) were dissolved in anhydrous methanol (10 ml), and stirred at room temperature for 30 minutes. To the mixture was added sodium cyanoboron hydride (in solid form) (0.24 g) over a period of 30 minutes and further stirred for 30 minutes. After the reaction solution was concentrated under reduced pressure, water and chloroform were added thereto, and the mixture was separated into layers. The organic layer was concentrated under reduced pressure, and subjected to column chromatograpy on silica gel and eluted with chloroform to give the desired product (0.42 g).

Workup

  1. stirringfurther stirred for 30 minutes
  2. concentrationAfter the reaction solution was concentrated under reduced pressure, water and chloroform
  3. additionwere added
  4. customthe mixture was separated into layers
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-66f527c241c141639f84e1e49de3ab41
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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