2-Methylbenzoic acid → 6-(2-Methoxy-4-methoxymethoxyphenyl)-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1043676Notes

Reaction equation

HRID 1043676 reaction equation
[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:27])=[CH:6][C:7]([CH3:26])([CH3:25])[NH:8]2.C[C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([OH:33])=O.[CH2:38](P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1.CCCCCC>[CH3:24][O:23][C:14]1[CH:15]=[C:16]([O:19][CH2:20][O:21][CH3:22])[CH:17]=[CH:18][C:13]=1[C:12]1[C:3]([CH2:2][O:1][C:31](=[O:33])[C:30]2[CH:29]=[CH:37][C:36]([CH3:38])=[CH:35][CH:34]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:26])([CH3:25])[CH:6]=[C:5]2[CH3:27]

Participants

7

Reactant 4

HCID 83732-Methylbenzoic acidHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 579905855-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 579905836-(2-Methoxy-4-methoxymethoxyphenyl)-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 73.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 1, 1.00 g, 2.71 mmol), 2-methylbenzoic acid (739 mg, 5.43 mmol), tri-n-butylphosphine (1.35 mL, 5.40 mmol), and 1,1′-(azodicarbonyl)dipiperidine (1.37 g, 5.43 mmol) were dissolved in anhydrous benzene (30 mL), and then the mixture was stirred under argon atmosphere at room temperature overnight. Hexane (30 mL) was added to the reaction mixture, and then the unsoluble materials were filtered out. The filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (967 mg) as a colorless amorphous product. (Yield 73%)

Workup

  1. filtrationthe unsoluble materials were filtered out
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c7da24d070c544b286c32d9c127d467c
Source dataset
uspto-grants-2013_10
Patent number
US08563551B2

Reaction notes

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