Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate → Methyl 4-(3-phenylacryloylamino)benzoate

HRID 2422937Notes

Reaction equation

HRID 2422937 reaction equation
[CH:1]1[C:10]2[C:5](=CC=CC=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]([NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23]C)=[O:21])=[CH:18][CH:17]=1)=[O:14]>Cl>[C:2]1([CH:11]=[CH:12][C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:25][CH:26]=2)=[O:14])[CH:1]=[CH:10][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67243223Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate

Product 1

HCID 675852Methyl 4-(3-phenylacryloylamino)benzoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

This was obtained as a white solid from cinnamoyl chloride (1.1 g, 6.62 mmol) and ethyl 4-aminobenzoate (1.10 g, 6.62 mmol) in a similar manner as described for preparation of 42. The reaction mixture was stirred at room temperature overnight and the mixture was poured in HCl (aq, 2N, 20 ml). The product was extracted with DCM (2×20 ml), dried over Na2SO4 and the solvent removed under reduced pressure. The crude amide 41 was used in the next step without further purification.

Workup

  1. extractionThe product was extracted with DCM (2×20 ml)
  2. dry with materialdried over Na2SO4
  3. customthe solvent removed under reduced pressure
  4. customThe crude amide 41 was used in the next step without further purification

Sources & evidence

ORD record
ord-4f825ae8d3534a5bba9a7c942e720f98
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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