HCID 25228381, compound → HCID 135858979, compound

HRID 1920684Notes

Reaction equation

HRID 1920684 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([Cl:20])[C:10]([O:16]COC)=[CH:11][CH:12]=2)[N:7]=1)(=[O:3])[CH3:2]>Cl.CO>[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([Cl:20])[C:10]([OH:16])=[CH:11][CH:12]=2)[N:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 25228381HCID 25228381, compound

Product 1

HCID 135858979HCID 135858979, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

Referring to FIG. 20, 12N HCl (1 drop) was added to a solution of 11c (0.0140 g, 0.0473 mmol) in methanol (3 mL), and the mixture stirred for 10 min. The solvent was evaporated, and the residue was purified by column chromatography (3:7 EtOAc/hexane) to afford CHQ-OAc (0.0042 g, 0.017 mmol, 35%) as a white solid (mp 126-127° C. dec): 1H NMR (CDCl3) δ 8.13 (1H, d, J=8.5 Hz), 7.68 (1H, d, J=8.5 Hz) 7.40 (1H, d, J=8.5 Hz) 7.34 (1H, d, J=9.0 Hz) 5.46 (2H, s), 2.23 (3H, s); 13C NMR (CDCl3) δ 171.0, 157.7, 153.2, 144.7, 137.4 127.6 123.8, 118.2, 117.8, 115.1, 67.5, 21.2; FTIR (neat) 2928, 1737, 1629, 1511, 1343, 1251, 850, 777 cm−1; MS (ESI) m/z calculated for (C12H10ClNO3+H)+ 252 (35Cl) and 254 (37Cl), found 252 (35Cl) and 254 (37Cl); HRMS (ESI) m/z calculated for (C12H10ClNO3+H)+ 252.0427 (35Cl) and 254.0398 (37Cl), found 252.0420 (35Cl) and 254.0390 (37Cl).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (3:7 EtOAc/hexane)
  3. customto afford CHQ-OAc (0.0042 g, 0.017 mmol, 35%) as a white solid (mp 126-127° C. dec)

Sources & evidence

ORD record
ord-9d0636df72d6446b85027e026c7b2cbb
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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