Hydrochloric Acid → HCID 67361412, compound

HRID 1951351Notes

Reaction equation

HRID 1951351 reaction equation
[CH3:1][C:2]1[CH2:18][N:5]2[CH:6]=[CH:7][C:8]3[C:9]([CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=3)=[C:4]2[N:3]=1.[OH-].[K+].Cl>C1COCC1.C(O)C>[CH3:1][C:2]1[CH2:18][N:5]2[CH:6]=[CH:7][C:8]3[C:9]([CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=3)=[C:4]2[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67361470HCID 67361470, compound

Product 1

HCID 67361412HCID 67361412, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 7b (240 mg, 0.99 mmol) in a mixture of THF (1 mL) and ethanol (1 mL) was added a 2N aqueous KOH solution (1 mL, 2 mmol). The solution was stirred at room temperature for 6 h. After cooling at 0° C., the reaction mixture was acidified at pH=1 by addition of concentrated hydrochloric acid. The solid was collected by filtration and dried at 60° C. under vacuum to give acid 15 (210 mg, 99%); mp 325-327° C.; IR (KBr) 3500-3300, 1714, 1669, 1251 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 2.52 (s, 3H), 7.51 (d, J=7.5 Hz), 7.67 (s, 1H), 8.04 (s, 1H), 8.54 (d, 1H, J=7.5 Hz), 13.18 (brs, 1H); 13C NMR (100 MHz, DMSO-d6) δ 10.1, 105.2, 106.8, 107.9, 112.2, 124.2, 129.8, 130.2, 135.4, 136.0, 161.5; MS m/z 215 (M+, 44), 197 (60), 171 (100), 170 (92), 143 (14), 117 (15). Anal. Calcd for C11H9N3O2: C, 61.39; H, 4.22; N, 19.53. Found: C, 61.71; H, 4.38; N, 19.61.

Workup

  1. temperatureAfter cooling at 0° C.
  2. filtrationThe solid was collected by filtration
  3. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-f3deaab9af3a4151b548606a15cf3e4f
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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