1,1'-(Diazomethylene)bis(benzene) → HCID 58928752, compound

HRID 853694Notes

Reaction equation

HRID 853694 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C:21]([C:23]1[C:24]([O:48][CH3:49])=[C:25]2[C:30](=[C:31]([O:37][Si](C(C)C)(C(C)C)C(C)C)[C:32]=1[C:33]([O:35][CH3:36])=[O:34])[N:29]=[CH:28][CH:27]=[CH:26]2)=[O:22].[C:50]1([C:56]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[N+]=[N-])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1COCC1>[CH3:19][O:20][C:21]([C:23]1[C:24]([O:48][CH3:49])=[C:25]2[C:30](=[C:31]([O:37][CH:56]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:32]=1[C:33]([O:35][CH3:36])=[O:34])[N:29]=[CH:28][CH:27]=[CH:26]2)=[O:22]

Participants

5

Reactant 3

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 2724141Tetrabutylammonium FluorideHCID 589290076,7-Dimethyl 5-methoxy-8-[[tris(1-methylethyl)silyl]oxy]-6,7-quinolinedicarboxylate

Product 1

HCID 58928752HCID 58928752, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of TBAF in THF (4 ml) was added to 5-methoxy-8-triisopropylsilanyloxy-quinoline-6,7-dicarboxylic acid dimethyl ester (0.85 g, 1.9 mmol) in 20 ml dry THF. The reaction was stirred at rt for 1 h, at which time the reaction mixture was concentrated and the residue dissolved in 100 mL diethyl ether and washed with 25 mL 1N HCl, followed by 25 mL of saturated aq. NaCl. The organic layer was concentrated and the residue was dissolved in 40 mL dichloroethane. Diphenyldiazomethane (0.7 g, 3.8 mmol) was added and the reaction temperature was raised to 70° C. for 24 h. The reaction mixture was concentrated and the residue chromatographed on silica gel (1/1 hexanes/EtOAc) to give 8-benzhydryloxy-5-methoxy-quinoline-6,7-dicarboxylic acid dimethyl ester (0.8 g, 61% yield overall). 1H NMR (CDCl3) δ 8.85 (d, 1H), 8.45 (d, 1H), 7.45 (dd, 1H), 3.98 (s, 3H), 3.85 (s, 3H), 3.74 (s, 3H); MS: 480 (M+Na).

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue dissolved in 100 mL diethyl ether
  3. washwashed with 25 mL 1N HCl
  4. concentrationThe organic layer was concentrated
  5. dissolutionthe residue was dissolved in 40 mL dichloroethane
  6. temperaturethe reaction temperature was raised to 70° C. for 24 h
  7. concentrationThe reaction mixture was concentrated
  8. customthe residue chromatographed on silica gel (1/1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-9d1649460adc40c99dc5f65bf34be258
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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