Hydrochloric Acid → HCID 22054607, compound

HRID 1374762Notes

Reaction equation

HRID 1374762 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=O)=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1.Cl.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:25])([F:26])[F:27])[CH:17]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 4311764Sodium borohydrideHCID 22054485HCID 22054485, compound

Product 1

HCID 22054607HCID 22054607, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-2-methyl-quinoline-7-carbaldehyde (example 13a, 180 mg, 0.875 mmol) in ethanol (3 mL) were added 4-amino-2-trifluoromethyl-benzonitrile (163 mg, 0.875 mmol), 25% aq. hydrochloric acid solution (1.5 mL), and sodium borohydride (207 mg, 5.25 mmol). The reaction mixture was stirred 16 h at r.t., then partitioned between ethyl acetate and 1 M aq. sodium hydroxide solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2, hexane/ethyl acetate 1:1 afforded the title compound (123 mg, 37%). Off-white solid, ISP-MS: m/e=376.3 ([M+H]+).

Workup

  1. custompartitioned between ethyl acetate and 1 M aq. sodium hydroxide solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-cf241d60be994b39ae36316666cdb9b3
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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