N-methyl-2-pyrrolidone → HCID 68556731, compound

HRID 2382021Notes

Reaction equation

HRID 2382021 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)#[N:4].C[N:15]1C(=O)CCC1>>[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([NH2:15])[CH:9]=[CH:8]2)#[N:4]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidone2×HCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

Product 1

HCID 68556731HCID 68556731, compoundYield 16%

Procedure

NaH (60%, 60 mmol) is portion-wise added to a solution of 5-cyano-1H-indole (20 mmol) in NMP (35 mL), and the reaction mixture is 0° C. for 1 h. A solution of HOSA (60 mmol) in NMP (14 mL) is added drop-wise at 0° C. The reaction mixture is warmed to rt and stirred overnight, then quenched with water and extracted with EtOAc. The organic layer is separated, washed with water three times and with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 20-40% EtOAc in heptane to afford 5-cyano-indole-1-ylamine (531 mg, 16%) as a solid. 1H NMR (300 MHz, CDCl3): δ 4.88 (br, 2N—H), 6.53 (d, H), 7.32 (d, H), 7.54 (q, 2H), 7.98 (d, H).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer is separated
  4. washwashed with water three times and with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with 20-40% EtOAc in heptane

Sources & evidence

ORD record
ord-ccb9a90ac4f74c06b1d1b8285034942c
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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