3,5-Heptanedione → HCID 11523520, compound

HRID 2104140Notes

Reaction equation

HRID 2104140 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[CH3:17][CH2:18][C:19](=O)[CH2:20][C:21](=[O:24])[CH2:22][CH3:23].[Na]>C(O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:19]([CH2:18][CH3:17])[C:20]([C:21](=[O:24])[CH2:22][CH3:23])=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 819233,5-HeptanedioneHCID 996772-Amino-5-bromobenzophenoneHCID 5360545Sodium

Product 1

HCID 11523520HCID 11523520, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared according to the general procedure of method A. The (2-Amino-5-bromo-phenyl)-phenyl-methanone [example A16] (on 0.1-1 g scale) and 3,5-heptanedione (1.5 equiv) and sodium tetrachloroaureate(III) dihydrate (0.025 equiv) were heated in parallel in a Radley carousel under nitrogen in ethanol (10% w/w-solution of (2-Amino-5-bromo-phenyl)-phenyl-methanone) and reacted for 24 h. The reaction mixture was evaporated to dryness and the residue purified by chromatography on silica gel in heptane/ethyl acetate (20:1). Yield: 37%. MS: m/z=368 (M).

Workup

  1. customreacted for 24 h
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue purified by chromatography on silica gel in heptane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-25fab1815f5e4638b226261b45007917
Source dataset
uspto-grants-2009_08
Patent number
US07576217B2

Reaction notes

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