Water → Methyl 1-amino-1H-indole-2-carboxylate

HRID 1261970Notes

Reaction equation

HRID 1261970 reaction equation
Cl[O-].[Na+].O.[CH3:5][O:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8].[OH-].[Na+].[Cl-].[NH4+:21]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].[OH-].[NH4+].COC(C)(C)C>[CH3:5][O:6][C:7]([C:9]1[N:10]([NH2:21])[C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8]

Participants

9

Reactant 5

HCID 962Water3×HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 70992Methyl 1H-indole-2-carboxylateHCID 23665760Sodium Hypochlorite

Product 1

HCID 57416054Methyl 1-amino-1H-indole-2-carboxylateYield 14,350.3%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 14923Ammonium HydroxideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A 2 M solution of sodium hypochlorite in water (200 mL, 0.40 mol) was added dropwise to a biphasic mixture of commercially available 1H-indole-2-carboxylic acid methyl ester (20.00 g, 0.11 mol), capriquat (4.5 mL, 0.01 mol), 7 M of sodium hydroxide in water (326 mL, 2.28 mol), 8 M of ammonium hydroxide in water (100 mL, 0.80 mol), ammonium chloride (37 g, 0.68 mmol), and 2-methoxy-2-methylpropane (318 mL). The reaction was worked up about 20 min after the addition was completed. The organic layer was separated and was washed with saturated aqueous sodium thiosulfate. Organic extracts were dried over magnesium sulfate, then filtered, and the solvent was evaporated in vacuum to afford 1-amino-1H-indole-2-carboxylic acid methyl ester (18.56 g, 85%), which was used in the next step without further purification. 1H-NMR (CDCl3) δ 7.62 (m, 2H), 7.36 (m, 1H), 7.18 (s, 1H), 7.13 (s, 1H), 5.32 (br s, 2H), 3.93 (s, 3H).

Workup

  1. additionafter the addition
  2. customThe organic layer was separated
  3. washwas washed with saturated aqueous sodium thiosulfate
  4. dry with materialOrganic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-95ba15e4d9cd4815a59f853cd7ad07af
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…