3-Chloro-4-(propan-2-yloxy)aniline → 4'-(Isopropoxy)-3'-chloro-1-methoxycyclopropanecarboxanilide

HRID 1862799Notes

Reaction equation

HRID 1862799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])[NH2:5].[CH3:13][O:14][C:15]1([C:18](OC)=[O:19])[CH2:17][CH2:16]1.C[O-].[Na+]>C1C=CC=CC=1>[CH:10]([O:9][C:8]1[CH:7]=[CH:6][C:4]([NH:5][C:18]([C:15]2([O:14][CH3:13])[CH2:17][CH2:16]2)=[O:19])=[CH:3][C:2]=1[Cl:1])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 65003943-Chloro-4-(propan-2-yloxy)anilineHCID 10942334Sodium MethoxideHCID 20393514Methyl 1-methoxycyclopropanecarboxylate

Product 1

HCID 203934954'-(Isopropoxy)-3'-chloro-1-methoxycyclopropanecarboxanilideYield 21.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture consisting of 5.6 g of 3-chloro-4-isopropoxyaniline, 3.9 g of methyl 1-methoxycyclopropanecarboxylate and 1.8 g of sodium methoxide in 50 ml of benzene was refluxed for 3 hours. The reaction mixture was concentrated to a volume of 25 ml, poured over ice water, acidified with hydrochloric acid and extracted with ether. The extract was dried, filtered and concentrated. Purification by silica chromatography gave 1.8 g of product as a white crystalline solid; m.p. 86°-87° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated to a volume of 25 ml
  3. additionpoured over ice water
  4. extractionextracted with ether
  5. customThe extract was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica chromatography

Sources & evidence

ORD record
ord-c074bb11e621450291b7f0814b895cf7
Source dataset
uspto-grants-1979_09
Patent number
US04166735

Reaction notes

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