HCID 19421811, compound → HCID 19421836, compound

HRID 744119Notes

Reaction equation

HRID 744119 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([CH:13]=[CH2:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]>C(OCC)(=O)C.[Pt]>[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([CH2:13][CH3:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 19421811HCID 19421811, compound

Product 1

HCID 19421836HCID 19421836, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A slurry of platinum on sulphide carbon (0.1 g) in ethyl acetate was added under nitrogen to a solution of the methyl 2-amino-4-chloro-6-vinylbenzoate (0.362 g) in ethyl acetate. This mixture was hydrogenated at 30 psi for 2 h. The catalyst was filtered off and the solvent removed in vacuo to leave the desired methyl 2-amino-4-chloro-6-ethylbenzoate as a yellow oil (0.34 g). δH (250 MHz, DMSO-d6) 1.08 (3H, t, J 7.5 Hz, CH2CH3), 2.60 (2H, q, J 7.5 Hz, CH2CH3), 3.81 (3H, s, CO2CH3), 5.85 (2H, s, NH2), 6.46 (1H, d, J 2.5 Hz, H-3 or H-5), 6.65 (1H, d, J 2.5 Hz, H-3 or H-5).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5e1e067865d441f0a0f060d0e3c08fa4
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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