Diethyl Oxalate → HCID 178470497, compound

HRID 1011920Notes

Reaction equation

HRID 1011920 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5](=O)[CH:6]([CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)=O)[CH3:2].BrC1C=C(C(=O)CC)C=CC=1.C(OCC)(=O)C(OCC)=O.O.[NH2:41][NH2:42]>CCO>[CH2:1]([O:3][C:4]([C:5]1[C:6]([CH3:16])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)[NH:42][N:41]=1)=[O:18])[CH3:2]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 24654Hydrazine hydrate (1:1)HCID 882721-Propanone, 1-(3-bromophenyl)-HCID 673147814-(3-Bromo-phenyl)-3-methyl-2,4-dioxo-butyric acid ethyl ester

Product 1

HCID 178470497HCID 178470497, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 16A], 4-(3-bromo-phenyl)-3-methyl-2,4-dioxo-butyric acid ethyl ester (synthesized from 3′-bromopropiophenone and diethyl oxalate, following a procedure described in Ksander, Gary M.; McMurry, John E.; Johnson, Mark. A method for the synthesis of unsaturated carbonyl compounds. Journal of Organic Chemistry (1977), 42(7), 1180-5) and hydrazine monohydrate were heated at 90° C. in EtOH for 1 h to give after crystallization (Et2O/n-penatane) the title compound in 46% yield as off-white powder. MS: 308.1 (M+, 1 Br).

Workup

  1. customto give
  2. customafter crystallization (Et2O/n-penatane) the title compound in 46% yield as off-white powder

Sources & evidence

ORD record
ord-43d9a13411b34aab856a32aa886ecb07
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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