Hydroxylamine → HCID 86652338, compound

HRID 1400680Notes

Reaction equation

HRID 1400680 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=2[O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22](OC)=[O:23])[CH:20]=3)[CH:15]=[CH:14]2)[CH2:3][CH2:2]1.[OH-:30].[Na+].[NH2:32]O.O>CO>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]2[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=2[O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([NH:32][OH:30])=[O:23])[CH:20]=3)[CH:15]=[CH:14]2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 14798Sodium HydroxideHCID 58213826HCID 58213826, compound

Product 1

HCID 86652338HCID 86652338, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(2-(2-(morpholinomethyl)phenoxy)ethyl)-1H-indole-6-carboxylate (0.3 g, 0.83 mmol) in methanol (25 mL) was added a premixed (5 min) solution of NaOH (0.24 g, 6 mmol) and NH2OH (50% wt/wt in H2O, 1 mL) and H2O (2 mL). After stirring 5 hr at room temperature, the solution was concentrated and then diluted with H2O (30 mL) and the pH was adjusted to ˜9 with 1N HCl. The mixture was then extracted with ethyl acetate (100 mL) and concentrated to ˜3 mL and allowed to sit at room temperature for 16 hr. The resulting solid was isolated by filtration to provide 96 mg (29%) of 1-(2-(2-(morpholinomethyl)phenoxy)ethyl)-N-hydroxy-1H-indole-6-carboxamide as a tan solid. 1H NMR (300 MHz, DMSO) δ 11.11 (s, 1H), 8.90 (s, 1H), 8.03 (s, 1H), 7.62-7.55 (m, 2H), 7.44 (d, 1H, J=8.2 Hz), 7.19 (m, 2H), 6.90 (m, 2H), 6.50 (d, 1H, J=3.0 Hz), 4.63 (t, 2H, J=5.2 Hz), 4.30 (t, 2H, J=5.2 Hz), 3.43 (m, 4H), 3.18 (s, 2H), 2.12 (m, 4H). EM (calc.): 395.18; MS (M+H): 396.04.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with H2O (30 mL)
  3. extractionThe mixture was then extracted with ethyl acetate (100 mL)
  4. concentrationconcentrated to ˜3 mL
  5. waitto sit at room temperature for 16 hr
  6. customThe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-fb2468ee3b6d4ffda782657c1545b3db
Source dataset
uspto-grants-2014_12
Patent number
US08906954B2

Reaction notes

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