4-(Trifluoromethyl)benzyl isocyanate → HCID 59216599, compound

HRID 2245298Notes

Reaction equation

HRID 2245298 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH:5]([OH:12])[CH2:6][NH:7]2.[F:13][C:14]([F:26])([F:25])[C:15]1[CH:24]=[CH:23][C:18]([CH2:19][N:20]=[C:21]=[O:22])=[CH:17][CH:16]=1>ClCCl>[OH:12][CH:5]1[CH2:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:21]([NH:20][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:26])[F:25])=[CH:24][CH:23]=2)=[O:22])[NH:7][CH2:6]1

Participants

4

Reactant 2

HCID 223376994-(Trifluoromethyl)benzyl isocyanateHCID 59216604HCID 59216604, compound

Product 1

HCID 59216599HCID 59216599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

5-Amino-1,2,3,4-tetrahydroquinolin-3-ol (36.4 mg, 0.22 mmol) is dissolved in dichloromethane and cooled to −20° C. 4-Trifluoromethylbenzylisocyanate (44.6 mg, 0.22 mmol) is added and the reaction mixture is warmed to room temperature over 4 h. The organic layer is diluted with dichloromethane, washed with aq. NH4Cl and water. The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness. The crude product consists of a mixture of regioisomers and is separated using preparative HPLC with an acetonitrile/water gradient.

Workup

  1. temperaturethe reaction mixture is warmed to room temperature over 4 h
  2. washwashed with aq. NH4Cl and water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. additionThe crude product consists of a mixture of regioisomers
  7. customis separated

Sources & evidence

ORD record
ord-18c9478f5e3f4398b45b4b7f59df1b4c
Source dataset
uspto-grants-2010_03
Patent number
US07683076B2

Reaction notes

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