Acetic Acid → HCID 70913324, compound

HRID 2208906Notes

Reaction equation

HRID 2208906 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:18](=O)[CH3:19].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:17][CH2:16][CH2:15]2)[CH2:18][CH3:19])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70874019HCID 70874019, compound

Product 1

HCID 70913324HCID 70913324, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 5-chloro-3-(cyclobutylamino)-2-methylbenzoate (0.70 g, 2.73 mmol) and acetaldehyde (0.36 g, 8.20 mmol) in dichloroethane (15 mL), acetic acid (0.98 g, 16.4 mmol) was added and the reaction stirred at room temperature for 10 minutes. Then sodium triacetoxyborohydride (1.7 g, 8.2 mmol) was added at 0° C. and the reaction stirred for 3 h at room temperature. On completion, the solvent was removed under reduced pressure to give title compound (0.71 g, 91%).

Workup

  1. stirringthe reaction stirred for 3 h at room temperature
  2. customOn completion, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8f7432f4184143cab915c9eed890ebbe
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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