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Methyl Acrylate → Methyl 2-acetamido-5-chlorocinnamate

HRID 358843
Notes
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Reaction equation

HRID 358843 reaction equation
C(OCCO)C.[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1I)(=[O:9])[CH3:8].C([O-])(=O)C.[K+].[C:24]([O:28][CH3:29])(=[O:27])[CH:25]=[CH2:26]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[CH:26]=[CH:25][C:24]([O:28][CH3:29])=[O:27])(=[O:9])[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 8076Glycol monoethyl etherHCID 517044Potassium AcetateHCID 15113903N-(4-chloro-2-iodophenyl)acetamide

Product 1

HCID 54287744Methyl 2-acetamido-5-chlorocinnamateYield 74.1%

Reagents, catalysts & solvents 3

HCID 11776
Triphenylphosphine
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 100 ml of ethylene glycol monoethyl ether were added 10 g of 2-acetylamino-5-chloroiodobenzene, 3.96 g of anhydrous potassium acetate, 2.84 g of methyl acrylate, 5.8 mg of palladium acetate and 17.4 mg of triphenylphosphine. The resulting mixture was allowed to react at 130° C. for 8 hours under the stream of a nitrogen gas. The reaction solution was cooled to 50° C. and poured into 300 ml of water, and then a large amount of white crystal precipitated. This crystal was filtered off, washed with water and vacuum-dried to obtain 6.2 g of methyl 2-acetylamino-5-chlorocinnamate. The yield was 72.5%.

Workup

  1. customto react at 130° C. for 8 hours under the stream of a nitrogen gas
  2. customa large amount of white crystal precipitated
  3. filtrationThis crystal was filtered off
  4. washwashed with water
  5. customvacuum-dried

Sources & evidence

ORD record
ord-cebbaeae27b945938b0c1f366dc5ecb3
Source dataset
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04997972

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes