2-Amino-2-phenylethan-1-ol → HCID 66763197, compound

HRID 578716Notes

Reaction equation

HRID 578716 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH:14]1[CH:19]=[CH:18][C:17]([C@H:20]([NH2:23])[CH2:21][OH:22])=[CH:16][CH:15]=1.Cl.[NH+]1C=CC=CC=1>COCCO.C(OCC)(=O)C>[OH:22][CH2:21][C@@H:20]([NH:23][C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)[C:17]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 1347972-Amino-2-phenylethan-1-olHCID 147925994-Chloroquinoline-8-carbonitrileHCID 21584435Pyridinium hydrochloride

Product 1

HCID 66763197HCID 66763197, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-Chloro-quinoline-8-carbonitrile (200 mg, 1.1 mmol), (S)-Phenylglycinol (160 mg, 1.2 mmol), pyridinium hydrochloride (138 mg, 1.2 mmol) in 2-methoxyethanol (3.5 mL) was placed in a microwave 150° C., 50 Watts for 2 h. The solution was diluted with ethyl acetate and washed with brine solution. Purification by silica gel (20-80% ethyl acetate/heptane) afforded 4-((S)-2-Hydroxy-1-phenyl ethylamino)-quinoline-8-carbonitrile (320 mg, 33%) as a white solid. LCMS (ESI) 290 (M+H).

Workup

  1. customwas placed in a microwave 150° C.
  2. washwashed with brine solution
  3. customPurification by silica gel (20-80% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-a3039664c4994700a82b9dbca1e49d53
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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