4-Chloroaniline → HCID 60994470, compound

HRID 1912484Notes

Reaction equation

HRID 1912484 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Br[C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 78124-ChloroanilineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 60994470HCID 60994470, compoundYield 32%

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloroaniline (2 g, 15.7 mmol), sodium bicarbonate (1.58 g, 18.8 mmol) and ethyl 2-bromo-2-methylpropanoate (6.12 g, 31.4 mmol) was heated at 140° C. in microwave reactor for 2 h. The reaction was cooled to rt and filtered. The filtrate was concentrated and purified by flash column chromatography using 0-40% EtOAc in heptanes as eluent. The product containing fractions were collected, concentrated, and dried under high vacuum overnight to give ethyl 2-(4-chlorophenylamino)-2-methylpropanoate (1.2 g, 32% yield) as an brown oil.

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash column chromatography
  5. additionThe product containing fractions
  6. customwere collected
  7. concentrationconcentrated
  8. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-d759e26654f846ff82c0e65dab9d89b3
Source dataset
uspto-grants-2013_12
Patent number
US08609664B2

Reaction notes

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