Hydrochloric Acid → HCID 68416291, compound

HRID 1438165Notes

Reaction equation

HRID 1438165 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([OH:12])[C:10]#[N:11].[CH3:13][OH:14].Cl>C(OCC)C.O1CCOCC1>[ClH:8].[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH:9]([OH:12])[C:10](=[NH:11])[O:14][CH3:13])[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59838024HCID 59838024, compound

Product 1

HCID 68416291HCID 68416291, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To 121A (640 mg, 3.48 mmol) in anhydrous diethyl ether (115 mL) at 0° C. was added MeOH (1.4 mL) and 4.0 N HCl in dioxane (3.5 mL). The mixture was stirred at 0° C. for 30 min and then at rt for 4 h. The solvent was removed to give methyl 2-(5-chloro-2-fluorophenyl)-2-hydroxyacetimidate HCl salt. To this salt in CH2Cl2 (10 mL) was added H2O (10 mL). The mixture was stirred at rt for 30 min, then extracted with CH2Cl2 (2×50 mL). The combined organic extracts were dried and concentrated. The crude product was purified by silica gel chromatography to give 121B (610 mg, 80% yield) as a viscous oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.55 (d, J=4.83 Hz, 1H) 3.80 (s, 3H) 5.38 (d, J=4.83 Hz, 1H) 7.03 (t, J=9.23 Hz, 1H) 7.27-7.31 (m, 1H) 7.39 (dd, J=6.15, 2.64 Hz, 1H).

Workup

  1. waitat rt for 4 h
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-8f3306e6b6034fb79b2167d65b7b58eb
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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