Hydrochloric Acid → HCID 72948622, compound

HRID 1050923Notes

Reaction equation

HRID 1050923 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[C:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1)(=O)C.Cl>CO.O>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[C:18]#[C:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[OH:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 90025094HCID 90025094, compound

Product 1

HCID 72948622HCID 72948622, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Potassium carbonate (0.48 g, 3.48 mmol, 2.0 eq.) was added to a stirred solution of 2-(quinolin-2-ylethynyl)phenyl acetate (0.50 g, 1.74 mmol, 1.0 eq.) in a 1:1 mixture of methanol-water (10 mL). The resulting mixture was stirred at r.t. for 3 h. The reaction was poured onto water (50 mL) and the pH was adjusted to 7.0 by careful addition of aqueous hydrochloric acid (10%). The mixture was extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate and were concentrated under reduced pressure yielding the product (0.42 g, 95%) as a pale yellow solid; 1H NMR (500 MHz, DMSO-d6) δ 6.87 (t, J=7.5 Hz, 1H, Ar), 6.97 (d, J=8.0 Hz, 1H, Ar), 7.30 (t, J=8.0 Hz, 1H, Ar), 7.50 (d, J=7.5 Hz, 1H, Ar), 7.63 (t, J=7.5 Hz, 1H, Ar), 7.69 (d, J=8.5 Hz, 1H, Ar), 7.81 (t, J=7.0 Hz, 1H, Ar), 8.00 (d, J=7.0 Hz, 1H, Ar), 8.01 (d, J=7.0 Hz, 1H, Ar), 8.40 (d, J=8.5 Hz, 1H, Ar), 10.23 (s, 1H, OH).

Workup

  1. additionThe reaction was poured onto water (50 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×25 mL)
  3. washThe combined organic extracts were washed with brine (25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-d1fb9595ef8c499bb4de34a44c6ab327
Source dataset
uspto-grants-2016_07
Patent number
US09388138B2

Reaction notes

Loading…