Sodium Hydroxide → HCID 86008531, compound

HRID 1096837Notes

Reaction equation

HRID 1096837 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH:9]=O)[CH:5]=[CH:4][N:3]=1.[CH:11]1([NH2:14])[CH2:13][CH2:12]1.[BH4-].[Na+].[OH-].[Na+]>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][NH:14][CH:11]2[CH2:13][CH2:12]2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 341809912-Chloro-3-methylpyridine-4-carbaldehyde

Product 1

HCID 86008531HCID 86008531, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-chloro-3-methylpyridine-4-carbaldehyde (58.35 g, 375 mmol) and cyclopropylamine (52.6 mL, 750 mmol) in MeOH (800 mL) was stirred overnight at rt. The mixture was cooled to 0° C. and NaBH4 (18.4 g, 488 mmol) was added portionwise. The mixture was stirred overnight at rt. Aq. 1M NaOH (250 mL) was added and the solvents were partially removed under reduced pressure. The aq. phase was extracted with EtOAc (3×). The combined org. phases were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification fy FC yielded the compound (54.56 g, 74%) as a pale yellow liquid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred overnight at rt
  3. customthe solvents were partially removed under reduced pressure
  4. extractionThe aq. phase was extracted with EtOAc (3×)
  5. washphases were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification

Sources & evidence

ORD record
ord-865b8c4504554680a9aaa3fd31a5ccb4
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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