Tributylphosphine → 7-[2-Methoxy-4-(2-methylbenzoyloxy)phenyl]-8-(2-methoxy-5-nitrophenoxymethyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038507Notes

Reaction equation

HRID 1038507 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])=[CH:18][C:17]=2[O:32][CH3:33])=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[NH:8]2.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][C:37]=1O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1CCN(C(/N=N/C(N2CCCCC2)=O)=O)CC1>O1CCCC1>[CH3:33][O:32][C:17]1[CH:18]=[C:19]([O:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH:20]=[CH:21][C:16]=1[C:4]1[C:3]([CH2:2][O:1][C:37]2[CH:38]=[C:39]([N+:42]([O-:44])=[O:43])[CH:40]=[CH:41][C:36]=2[O:35][CH3:34])=[C:12]2[C:7]([NH:8][C:9]([CH3:14])([CH3:15])[C:10](=[O:13])[NH:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 13831Tributylphosphine3×HCID 694712-Methoxy-5-nitrophenol3×HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 689266918-Hydroxymethyl-7-[2-methoxy-4-(2-methylbenzoyloxy)phenyl]-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 576719137-[2-Methoxy-4-(2-methylbenzoyloxy)phenyl]-8-(2-methoxy-5-nitrophenoxymethyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-hydroxymethyl-7-[2-methoxy-4-(2-methylbenzoyloxy)phenyl]-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 23, 40.1 mg, 0.0898 mmol), 2-methoxy-5-nitrophenol (22.8 mg, 0.135 mmol), and tri n-butylphosphine (33.7 μL, 0.135 mmol) was dissolved in anhydrous tetrahydrofuran (1 mL), 1,1′-(azodicarbonyl)dipiperidine (34.0 mg, 0.135 mmol) was added thereto, and then the mixture was stirred at room temperature. After 20 minutes, 2-methoxy-5-nitrophenol (23.1 mg, 0.137 mmol), tri n-butylphosphine (33.7 μL, 0.135 mmol), and 1,1′-(azodicarbonyl)dipiperidine (33.9 mg, 0.134 mmol) were added thereto, and after 80 minutes, 2-methoxy-5-nitrophenol (22.9 mg, 0.135 mmol), tri-n-butylphosphine (33.7 μL, 0.135 mmol), and 1,1-(azodicarbonyl)dipiperidine (34.0 mg, 0.135 mmol) were added further. The stir was stopped 3 hours later and the reaction mixture was concentrated. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (22.1 mg) as a pale yellow amorphous product. (Yield 41%)

Workup

  1. waitafter 80 minutes
  2. waitThe stir was stopped 3 hours
  3. concentrationlater and the reaction mixture was concentrated
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2bad87a6648c451d849d4eefd2f806d2
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

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