Sodium Hydroxide → 1,3,3-Trimethyl-2,3-dihydro-1H-indol-5-amine

HRID 392862Notes

Reaction equation

HRID 392862 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH2:8][C:7]2([CH3:15])[CH3:14])([O-])=O.[OH-].[Na+]>Cl>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH2:8][C:7]2([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22662107HCID 22662107, compound

Product 1

HCID 226621081,3,3-Trimethyl-2,3-dihydro-1H-indol-5-amineYield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Nitro-1,3,3-trimethyl-indoline (8.16 g, 40 mmole) was added to a solution of stannous chloride (53 g, 280 mmole) in 200 ml hydrochloric acid with stirring. The mixture was gently refluxed for 16 hrs. The cold reaction mixture was poured onto crushed ice, made alkaline with a concentrated solution of sodium hydroxide and extracted with ethyl acetate (4×200 ml). The combined ethyl acetate solutions were dried with anhydrous sodium sulphate and decolorized with a small amount of active carbon. Solvent was removed and the residue re-crystallized from ethyl acetate to 5.96 g of a yellow solid, an 80% yield of 5-amino-1,3,3-trimethyl-indoline.

Workup

  1. temperatureThe mixture was gently refluxed for 16 hrs
  2. customThe cold reaction mixture
  3. additionwas poured
  4. customonto crushed ice
  5. extractionextracted with ethyl acetate (4×200 ml)
  6. dry with materialThe combined ethyl acetate solutions were dried with anhydrous sodium sulphate
  7. customSolvent was removed
  8. customthe residue re-crystallized from ethyl acetate to 5.96 g of a yellow solid

Sources & evidence

ORD record
ord-f083af05388a4d5d8aa8f3ddff6b5c41
Source dataset
uspto-grants-2004_10
Patent number
US06803471B2

Reaction notes

Loading…