Ethylamine → HCID 66599330, compound

HRID 1909020Notes

Reaction equation

HRID 1909020 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:18]=O)[CH:17]=2)[CH:5]=1.[CH2:21]([NH2:23])[CH3:22].[BH4-].[Na+]>CO.ClCCl>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][NH:23][CH2:21][CH3:22])[CH:17]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 4311764Sodium borohydrideHCID 86664345HCID 86664345, compound

Product 1

HCID 66599330HCID 66599330, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-Cyano-3-(5-formyl-pyridin-3-yl)-benzoic acid methyl ester (0.445 g, 1.67 mmol) was suspended in MeOH/dichloromethane (1:1; 8 mL) and a solution of ethylamine (2M in MeOH, 1.25 mL, 2.51 mmol) was added. The mixture was stirred for 16 hours at room temperature. The mixture was then was cooled to 0° C. and NaBH4 (76 mg, 2.01 mmol) was added in portions over 10 minutes. After allowing the mixture to warm to room temperature over 2 h, the reaction was quenched with 1 mL of water. The solution was concentrated in vacuo to ⅓ of its original volume and then it was partitioned between H2O and EtOAc. The aqueous phase was extracted with EtOAc (×2) and the combined organics were dried (Na2SO4) filtered and the solvent removed in vacuo to give 4-cyano-3-(5-ethylaminomethyl-pyridin-3-yl)benzoic acid methyl ester as a yellow oil (0.353 g, 72%). MS(ESI) m/z 296.0 (M+H)+.

Workup

  1. temperatureThe mixture was then was cooled to 0° C.
  2. temperatureto warm to room temperature over 2 h
  3. customthe reaction was quenched with 1 mL of water
  4. concentrationThe solution was concentrated in vacuo
  5. customit was partitioned between H2O and EtOAc
  6. extractionThe aqueous phase was extracted with EtOAc (×2)
  7. dry with materialthe combined organics were dried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-88124ec01f834b18b8035d67e7bc45fb
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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