Water → HCID 59401376, compound

HRID 2060893Notes

Reaction equation

HRID 2060893 reaction equation
[Cl:1][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.CC(C[AlH]CC(C)C)C.O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.CCOC(C)=O.CO>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:12][NH2:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14487Diisobutylaluminum hydride2×HCID 25517Ammonium ChlorideHCID 147925994-Chloroquinoline-8-carbonitrile

Product 1

HCID 59401376HCID 59401376, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

To 4-chloroquinoline-8-carbonitrile (Preparation 88) (422 mg 2.24 mmol) in toluene (20 mL) at −78° C. was added dropwise DIBAL-H (6.73 mL/1M solution in toluene, 6.73 mmol). After 20 min at −78° C. the mixture was allowed to warm to −40° C. The reaction mixture was then re-cooled to −78° C. and DIBAL-H (2.0 mL/1M solution in toluene, 2.0 mmol) was added. After 1 h water (1 mL), MeOH (5 mL) and then NH4Cl(aq) (10 mL) were added. After addition of EtOAc (20 mL) the mixture was stirred vigorously for 14 h at rt. The mixture was extracted with EtOAc (3×20 mL) and the combined organic phase washed with brine (20 mL) and dried (MgSO4). Solvent removed in vacuo to give the title compound: RT=2.10 min; m/z (ES+)=193.0 [M+H]+.

Workup

  1. temperatureThe reaction mixture was then re-cooled to −78° C.
  2. extractionThe mixture was extracted with EtOAc (3×20 mL)
  3. washthe combined organic phase washed with brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent removed in vacuo

Sources & evidence

ORD record
ord-2a3dc015848c45adb681c7ab2af78b2d
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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