Hydrochloric Acid → HCID 72948623, compound

HRID 1050924Notes

Reaction equation

HRID 1050924 reaction equation
[ClH:1].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]>C(OCC)C>[ClH:1].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72948622HCID 72948622, compound

Product 1

HCID 72948623HCID 72948623, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of hydrochloric acid (2.0 M in diethyl ether, 0.40 mL, 0.82 mmol, 1.0 eq.) was added dropwise to a stirred suspension of 2-(quinolin-2-ylethynyl)phenol (200 mg, 0.82 mmol, 1.0 eq.) in dry diethyl ether (10 mL). The mixture was stirred at r.t. for 30 min and was filtered. The solids were washed with diethyl ether (3×5 mL) and were dried under reduced pressure yielding the product (197 mg, 85% yield) as a bright yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 6.89 (t, J=7.5 Hz, 1H, Ar), 7.03 (d, J=8.0 Hz, 1H, Ar), 7.33 (t, J=8.0 Hz, 1H, Ar), 7.54 (d, J=7.5 Hz, 1H, Ar), 7.71 (t, J=7.5 Hz, 1H, Ar), 7.81 (d, J=8.5 Hz, 1H, Ar), 7.90 (t, J=7.0 Hz, 1H, Ar), 8.09 (d, J=8.0 Hz, 1H, Ar), 8.10 (d, J=8.0 Hz, 1H, Ar), 8.59 (d, J=8.5 Hz, 1H, Ar), 10.42 (br s, 1H, OH).

Workup

  1. filtrationwas filtered
  2. washThe solids were washed with diethyl ether (3×5 mL)
  3. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-946794ef7ebb4e99a1644fcbf201544b
Source dataset
uspto-grants-2016_07
Patent number
US09388138B2

Reaction notes

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