Sodium Hydroxide → Ethyl 5-amino-n-(3,4-dichlorobenzyl)indole-2-carboxylate

HRID 967103Notes

Reaction equation

HRID 967103 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:20]([O:22][CH2:23][CH3:24])=[O:21].[OH-].[Na+]>C(O)C>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][C:6]1[CH:25]=[CH:26][C:27]([Cl:28])=[C:4]([Cl:3])[CH:5]=1)[C:9]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:10]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22310852Ethyl n-(3,4-dichlorobenzyl)-5-nitroindole-2-carboxylate

Product 1

HCID 22310970Ethyl 5-amino-n-(3,4-dichlorobenzyl)indole-2-carboxylateYield 10.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium borohydride (1.19 g) in ethanol was added dropwise to ethyl N-(3,4-dichlorobenzyl)-5-nitroindole-2-carboxylate (12.4 g) and stannous chloride dihydrate (35.6 g) in ethanol at 60° C. and reaction stirred for 5 hours. The mixture was then cooled, made basic with 2N sodium hydroxide and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated to give an oil which crystallised upon trituration with i-hexane. Filtration yielded the desired end product as a pale brown solid (1.18 g, 10%); NMR δ (CDCl3) 1.32 (t, 3H), 4.26 (q, 2H), 6.69 (s, 2H), 6.78-7.35 (m, 7H); M/z (−) 363 (M+), 274, 267, 265, 151, 121, 102.

Workup

  1. customreaction
  2. temperatureThe mixture was then cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give an oil which
  7. customcrystallised upon trituration with i-hexane
  8. filtrationFiltration

Sources & evidence

ORD record
ord-20e5408273304a2daf451ee818088f96
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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