Sodium Hydroxide → 2-Methyl-1h-indol-6-amine

HRID 401249Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OC(C1NC2C(C=1)=C([N+]([O-])=O)C=CC=2)=O)C.C(O[C:27]([C:29]1[NH:30][C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[C:33]([N+:38]([O-])=O)[CH:32]=2)=O)C.[OH-].[Na+]>C1COCC1.O>[CH3:27][C:29]1[NH:30][C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[C:33]([NH2:38])[CH:32]=2

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LiAlH4 (7.8 g, 0.21 mol) in THF (300 mL) was added dropwise a mixture of 4-nitro-1H-indole-2-carboxylic acid ethyl ester and 6-nitro-1H-indole-2-carboxylic acid ethyl ester (B-4-b) (6 g, 25.7 mmol) in THF (50 mL) at 0° C. under N2. The mixture was heated at reflux overnight and then cooled to 0° C. H2O (7.8 mL) and 10% NaOH (7.8 mL) were added to the mixture at 0° C. The insoluble solid was removed via filtration. The filtrate was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography to afford 2-methyl-1H-indol-6-ylamine (B-4) (0.3 g, 8%). 1H NMR (CDCl3) δ 7.57 (br s, 1H), 7.27 (d, J=8.8 Hz, 1H), 6.62 (s, 1H), 6.51-6.53 (m, 1H), 6.07 (s, 1H), 3.59-3.25 (br s, 2H), 2.37 (s, 3H); ESI-MS 147.2 m/z (MH+).

Workup

additionwas added dropwise
temperatureThe mixture was heated
temperatureat reflux overnight
customThe insoluble solid was removed via filtration
dry with materialThe filtrate was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by column chromatography

Sources & evidence

ORD record: ord-194295caa1d1414dad1296fe0db1642f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741925B2

Reaction notes

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