4'-Bromoacetanilide → Ethyl 3-(4-acetamidophenyl)prop-2-enoate

HRID 1284862Notes

Reaction equation

HRID 1284862 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)=[O:3].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>>[C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:14]=[CH:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][CH:6]=1)(=[O:3])[CH3:1]

Participants

3

Reactant 2

HCID 76834'-BromoacetanilideHCID 8821Ethyl Acrylate

Product 1

HCID 53715054Ethyl 3-(4-acetamidophenyl)prop-2-enoateYield 10.4%

Procedure

The procedure described in Example 26 is repeated, but using 5.35 g (25 mmols) of 4-bromoacetanilide and 2.99 ml (27.5 mmols) of ethyl acrylate. After a reaction time of 12 hours at 130° C. and working up as described in Example 1, recrystallisation of the crude product from toluene gives 0.60 g (2.6 mmols) of ethyl 4-(N-acetylamino)-cinnamate as pale yellow crystals of melting point 133° C.; yield 10% of theory (conversion figure 1000; Pd content 0.01 mol %). Analysis for C13H15NO3 (molecular weight 233): calculated C 66.92; H 6.48; N 6.01; O 20.59, found C 66.52; H 6.38; N 6.07; O 20.59.

Workup

  1. customAfter a reaction time of 12 hours
  2. customat 130° C.
  3. customas described in Example 1, recrystallisation of the crude product from toluene

Sources & evidence

ORD record
ord-d4a452bc0dce4f7c8ef88cf56f9cd52a
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

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