Acetic Acid → 1-(8-Acetoxy-9-bromononyl)-3,7-dimethylxanthine

HRID 356612Notes

Reaction equation

HRID 356612 reaction equation
[OH:1][CH:2]([CH2:23]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12].[BrH:25].[C:26]([OH:29])(=O)[CH3:27].C(=O)(O)[O-].[Na+]>ClCCl.O>[C:26]([O:1][CH:2]([CH2:23][Br:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])(=[O:29])[CH3:27]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 98408081-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

Product 1

HCID 153385971-(8-Acetoxy-9-bromononyl)-3,7-dimethylxanthineYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (428 mg, 1.3 mmol) and 30% hydrogen bromide in acetic acid (0.8 ml, 3.9 mmol) was stirred for 90 minutes. The solution was poured into a mixture of water (10 ml), sodium bicarbonate (1.35 g), and dichloromethane (10 ml). After 10 minutes of vigorous stirring the layers were separated and the aqueous portion was extracted with dichloromethane (3×15 ml). The combined organic phases were dried over sodium sulfate and the solvent was evaporated under vacuum to give 1-(8-acetoxy-9-bromononyl)-3,7-dimethylxanthine (550 mg, 96% yield) as a yellow oil. Without further purification, the oil was dissolved in methanol (5 ml) and then a 1M solution of sodium methoxide in methanol (1.4 ml) was added. After 30 minutes the reaction mixture was poured into water (30 ml) and extracted with dichloromethane (3×40 ml). The combined organic phases were dried over sodium sulfate and the solvents evaporated under vacuum. The solid residue was recrystallized (dichloromethane-petroleum ether) to give 1-(8,9-oxidononyl)-3,7-dimethylxanthine (380 mg, 91% yield).

Workup

  1. stirringAfter 10 minutes of vigorous stirring the layers
  2. customwere separated
  3. extractionthe aqueous portion was extracted with dichloromethane (3×15 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-5fa59b946fee4b1091d66360848537b1
Source dataset
uspto-grants-1998_11
Patent number
US05837703

Reaction notes

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