Dimethylamine → HCID 43091262, compound

HRID 1750879Notes

Reaction equation

HRID 1750879 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH3:13][NH:14][CH3:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][N:14]([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 729332-Chloro-5-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43091262HCID 43091262, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-chloro-5-nitrobenzaldehyde (1 g, 5.39 mmol) was dissolved in THF (10 mL), and added with dimethylamine (2 M THF solution, 2.7 mL, 5.39 mmol). The reaction solution was cooled to 0° C., and NaBH(OAc)3 (1.6 g, 7.55 mmol) was slowly added thereto, followed by stirring for 12 hours or more at room temperature. The reaction mixture was added with water, and subjected to extraction with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (940 mg, 81%).

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed2cdb6902f4418c9ccd72b2838342ec
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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