Bromomethyl 3-methoxyphenyl ketone → 2-Amino-3-ethoxycarbonyl-5-(3-methoxy-phenyl)-1H-pyrrole

HRID 369848Notes

Reaction equation

HRID 369848 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH2:6][C:7](=[NH:9])[NH2:8])[CH3:3].C([O-])C.[Na+].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=O>C(O)C>[NH2:9][C:7]1[NH:8][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[CH:16][C:6]=1[C:5]([O:4][CH2:2][CH3:3])=[O:10]

Participants

5

Reactant 3

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 2723922Sodium ethoxideHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

Product 1

HCID 232827322-Amino-3-ethoxycarbonyl-5-(3-methoxy-phenyl)-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Analogously to Step 8.1, 14.5 g (87 mmol) of 2-amidino-acetic acid ethyl ester hydro-chloride in 150 ml of abs. ethanol are reacted with 5.9 g (87 mmol) of sodium ethanolate and 10.3 g (44 mmol) of 2-bromo-1-(3-methoxy-phenyl)-ethan-1-one (2-bromo-3'-methoxy-acetophenone; Janssen) to form the title compound; m.p. 96-97oC; TLC-Rf =0.2 (hexane/ethyl acetate [2:1]).

Sources & evidence

ORD record
ord-1e6174638c374ddca4eafe2c8c0c7541
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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