Stannous chloride dihydrate → HCID 57470208, compound

HRID 1908506Notes

Reaction equation

HRID 1908506 reaction equation
[C:1]([C:5]1[C:6]([N+:19]([O-])=O)=[CH:7][C:8]([N+]([O-])=O)=[C:9](/[CH:11]=[CH:12]/[N:13](C)C)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl>C(O)C>[C:1]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][C:6]=1[NH2:19])[NH:13][CH:12]=[CH:11]2)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 59129370HCID 59129370, compound

Product 1

HCID 57470208HCID 57470208, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (E)-2-(5-tert-butyl-2,4-dinitrophenyl)-N,N-dimethylethen-amine (5.3 g, 18 mmol) and tin (II) chloride dihydrate (37 g, 0.18 mol) in ethanol (200 mL) was heated at reflux overnight. The mixture was cooled to room temperature and the solvent was removed under vacuum. The residual slurry was diluted with water (500 mL) and was basifed with 10% aq. Na2CO3 to pH 8. The resulting suspension was extracted with ethyl acetate (3×100 mL). The ethyl acetate extract washed with water and brine, dried over Na2SO4, and concentrated. The residual solid washed with CH2Cl2 to afford a yellow powder, which was purified by column chromatography to give 5-tert-butyl-1H-indol-6-amine (0.40 g, 12%). 1H NMR (DMSO-d6) δ 10.34 (br s, 1H), 7.23 (s, 1H), 6.92 (s, 1H), 6.65 (s, 1H), 6.14 (s, 1H), 4.43 (br s, 2H), 2.48 (s, 9H); MS (ESI) m/e (M+H+) 189.1.

Workup

  1. temperatureat reflux overnight
  2. customthe solvent was removed under vacuum
  3. additionThe residual slurry was diluted with water (500 mL)
  4. extractionThe resulting suspension was extracted with ethyl acetate (3×100 mL)
  5. extractionThe ethyl acetate extract
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. washThe residual solid washed with CH2Cl2
  10. customto afford a yellow powder, which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-44696b768a9f40b1a283916d9a782fdf
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

Loading…