5-Methylcyclohexane-1,3-dione → HCID 67041612, compound

HRID 1929287Notes

Reaction equation

HRID 1929287 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[NH:14]C.[CH3:16][CH:17]1[CH2:22][C:21](=[O:23])[CH2:20][C:19](=O)[CH2:18]1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH2:14][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:9]=[CH:10][C:2]=1[Cl:1])[C:6]([O:8][C:19]1[CH2:18][CH:17]([CH3:16])[CH2:22][C:21](=[O:23])[CH:20]=1)=[O:7]

Participants

6

Reactant 3

HCID 4580955-Methylcyclohexane-1,3-dioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67041952HCID 67041952, compound

Product 1

HCID 67041612HCID 67041612, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

250 mg (1.1 mmol) of 4-chloro-3-(methylamino)-2-nitrobenzoic acid, 410.3 mg (3.3 mmol) of 5-methylcyclohexane-1,3-dione, 275.7 mg (1.4 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 13.5 mg (0.1 mmol) of 4-(dimethylamino)pyridine were dissolved in 6 ml of methylene dichloride and stirred at RT for 8 h. This was followed by washing with water and saturated NaHCO3 solution, after which the organic phase was dried over MgSO4 and then the whole was filtered through a small glass frit filled with 1 cm of silica gel, with suction, and the filter product was washed with heptane/ethyl acetate 1:2. The filtrate was concentrated.

Workup

  1. washby washing with water and saturated NaHCO3 solution
  2. dry with materialafter which the organic phase was dried over MgSO4
  3. filtrationthe whole was filtered through a small glass frit
  4. additionfilled with 1 cm of silica gel, with suction
  5. washthe filter product was washed with heptane/ethyl acetate 1:2
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-454ef67d594f4be79607d9bcf1827d37
Source dataset
uspto-grants-2012_05
Patent number
US08188002B2

Reaction notes

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