Acetic Acid → HCID 22054562, compound

HRID 1374772Notes

Reaction equation

HRID 1374772 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([CH:26]=O)=[CH:23][CH:24]=2)[N:19]=[C:18]([CH3:28])[CH:17]=1.[NH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1.C(O)(=O)C>ClCCCl>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][NH:29][C:30]3[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=3)=[CH:23][CH:24]=2)[N:19]=[C:18]([CH3:28])[CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 133964-AminobenzonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 22054485HCID 22054485, compound

Product 1

HCID 22054562HCID 22054562, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (74 mg, 0.34 mmol) was added to a solution of 4-chloro-2-methyl-quinoline-7-carbaldehyde (example 13a, 50 mg, 0.24 mmol), 4-aminobenzonitrile (29 mg, 0.24 mmol), and acetic acid (88 mg, 1.5 mmol) in 1,2-dichloroethane (0.5 mL), then after 16 h the reaction mixture was partitioned between ethyl acetate and 2 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 (48 mg, 64%). White solid, ISP-MS: m/e=308.2 ([M+H]+).

Workup

  1. customafter 16 h the reaction mixture was partitioned between ethyl acetate and 2 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-e74ce5c5a8a84228a58846ab88d11d14
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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