Hydrochloric Acid → HCID 20742869, compound

HRID 1884403Notes

Reaction equation

HRID 1884403 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:11]=2[N+:13]([O-:15])=[O:14])[CH2:6][CH2:5]1)(=O)C.Cl>CO.O>[N+:13]([C:11]1[CH:10]=[C:9]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:8]=[C:7]2[C:12]=1[NH:4][CH2:5][CH2:6]2)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12012757HCID 12012757, compound

Product 1

HCID 20742869HCID 20742869, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 16 (417 mg, 1.5 mmol) in a mixture of methanol (25 mL), water (5 mL) and conc. HCl (2.5 mL) was heated under reflux for 4 h. The solution was diluted with water (7 mL) and extracted with EtOAc. The combined organic phases were washed with brine, dried and evaporated to give a viscous oil. Trituration with ether and recrystallization (Et2O-hexanes) afforded 12 as red microcrystals (255 mg, 72%), mp 113-115° C.; UV: λmax (EtOH)/nm 246 (ε/M−1cm−1 16 600), 431 (5600); λmax [EtOH-25 mM Na phosphate, pH 7.0 (1:40)]/nm 238 (ε/M−1cm−1 16 400), 289 (6060), 450 (5060); IR: νmax/cm−1 3420, 3380, 1740, 1645, 1600, 1520; 1H NMR: δH (90 MHz) 7.64 (br s, 1H), 7.16 (br s, 1H), 6.71 (br s, 1H), 3.87 (t, J=8.3 Hz, 2H), 3.69 (s, 3H), 3.51 (s, 2H) and 3.15 (t, J=8.3 Hz, 2H). Anal. Calcd for C11H12N2O4: C, 55.93; H, 5.12; N, 11.85. Found: C, 55.74; H, 5.07; N, 11.68.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. customevaporated
  7. customto give a viscous oil
  8. customTrituration with ether and recrystallization (Et2O-hexanes)

Sources & evidence

ORD record
ord-ad8efe0b2fde4fe8957c3aae56bce0a3
Source dataset
uspto-grants-2004_07
Patent number
US06765014B1

Reaction notes

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