Carbon Dioxide → HCID 11436553, compound

HRID 1745826Notes

Reaction equation

HRID 1745826 reaction equation
C([N-]C(C)C)(C)C.[Li+].CC(C)([O-])C.[K+].[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]=[CH:22][CH:21]=[C:20]2[CH3:29].[C:30](=[O:32])=[O:31].Cl.N1C=CC=CC=1>C1COCC1>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]=[CH:22][CH:21]=[C:20]2[CH2:29][C:30]([OH:32])=[O:31]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 2724682Lithium diisopropylamideHCID 10176127Pyridinium chlorideHCID 10998092HCID 10998092, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11436553HCID 11436553, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium diisopropylamide (2M pentane solution 2.46 ml, 4.92 mmol) and potassium t-butoxide (0.552 g, 4.92 mmol) are added to THF (10 ml) at −70° C., followed by 6,7-dimethoxy-4-methyl-quinoline [J. Org. Chem., 1997, 623, 568 ] (1.0 g, 4.92 mmol). After 1 hour the reaction is poured on to an excess of crushed dry ice and warmed to room temperature overnight. Pyridine hydrochloride (0.57 g, 4.92 mmol) is added and the reaction partitioned between ether and water. The aqueous phase is evaporated, taken into hot methanol, treated with charcoal, filtered through celite and evaporated to afford (6,7-dimethoxy-quinolin-4-yl)-acetic acid, MH+ 248. This intermediate is then converted to the xanthine acording to the general procedure of Method C, mp >250° C.

Workup

  1. customthe reaction partitioned between ether and water
  2. customThe aqueous phase is evaporated
  3. additiontreated with charcoal
  4. filtrationfiltered through celite
  5. customevaporated

Sources & evidence

ORD record
ord-43560fbbd478434f83bddc6b058adb02
Source dataset
uspto-grants-2006_03
Patent number
US07019136B2

Reaction notes

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