Ethanol → HCID 118076414, compound

HRID 1051637Notes

Reaction equation

HRID 1051637 reaction equation
[Br:1][C:2]1[C:3]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:18]=2[F:26])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:15])[CH2:6][CH2:5]2.[Cl-].[NH4+].O1CCCC1.C(O)C>[Fe].O>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:3]2[C:2]([Br:1])=[CH:11][CH:10]=[C:9]3[C:4]=2[CH2:5][CH2:6][C@H:7]([CH3:15])[N:8]3[C:12](=[O:14])[CH3:13])=[C:18]([F:26])[CH:19]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 118076268HCID 118076268, compound

Product 1

HCID 118076414HCID 118076414, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 100-mL round-bottom flask was purged and maintained with an inert atmosphere of nitrogen, and charged with 1-[(2S)-6-bromo-5-(2-fluoro-4-nitrophenoxy)-2-methyl-1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-one (500 mg, 1.18 mmol), iron powder (331 mg, 5.91 mmol), ammonium chloride (128 mg, 2.37 mmol), tetrahydrofuran (9 mL), ethanol (3 mL), and water (9 mL). The resulting mixture stirred for 12 h at 80° C. and was then filtered. The filtrate was concentrated, and the residue was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 1-[(2S)-5-(4-amino-2-fluorophenoxy)-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-one (370 mg, 80%) as a light brown solid. MS (ESI, pos. ion) m/z 393, 395 [M+H]+.

Workup

  1. customA 100-mL round-bottom flask was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationwas then filtered
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9180608d30724844999411a499bae9a0
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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