Acetic Acid → HCID 70874019, compound

HRID 2208904Notes

Reaction equation

HRID 2208904 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:14]1(=O)[CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:12][C:10]1[CH:11]=[C:2]([NH:1][CH:14]2[CH2:17][CH2:16][CH2:15]2)[C:3]([CH3:13])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68295455Methyl 3-amino-5-chloro-2-methylbenzoate

Product 1

HCID 70874019HCID 70874019, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate (2.0 g, 10 mmol) and cyclobutanone (1.4 g, 20 mmol) in dichloroethane (20 mL), acetic acid (3.6 g, 60 mmol) was added and reaction stirred at room temperature for 10 minutes. Then sodium triacetoxyborohydride (6.3 g, 30 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 and the crude material was purified by column chromatography to afford the title compound (1.4 g, 56%).

Workup

  1. customreaction
  2. stirringthe reaction stirred for 3 h at room temperature
  3. customOn completion, the solvent was removed under reduced pressure
  4. customthe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-15ddcea3f35a4c10a769cef40a7761b8
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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