Hydrochloric Acid → HCID 59395045, compound

HRID 383359Notes

Reaction equation

HRID 383359 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([C:18]([F:21])([F:20])[F:19])=[CH:11][C:10]=1[CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C.[Fe]>[CH2:1]([O:8][C:9]1[C:10]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:11][C:12]([C:18]([F:21])([F:19])[F:20])=[C:13]([CH:14]=1)[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59394965HCID 59394965, compound

Product 1

HCID 59395045HCID 59395045, compoundYield 109.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-(benzyloxy)-2-cyclopentyl-5-nitro-4-(trifluoromethyl)benzene (3.0 g, 8.2 mmol) and Fe (2.8 g, 49.3 mmol) in 25% aqueous ethanol (40 mL) was added concentrated HCl (2.1 g, 1.8 mL, 58.7 mmol). The mixture was stirred at 50° C. for 4 h. The reaction was filtered hot and washed with ethanol (2×5 mL). The filtrate was concentrated to ˜20 mL volume, resulting in the precipitation of a yellow crystalline solid. The solid was filtered, washed with water and dried to provide 5-(benzyloxy)-4-cyclopentyl-2-(trifluoromethyl)aniline as a yellow-brown crystalline solid (3.0 g, 98% yield). NMR (400.0 MHz, CDCl3) δ 7.40-7.35 (m, 5H), 7.25 (d, J=6.7 Hz, 1H), 6.24 (s, 1H), 5.06 (s, 2H), 4.03 (s, 2H), 3.28-3.20 (m, 1H), 1.99-1.95 (m, 2H), 1.74-1.65 (m, 2H), 1.67-1.62 (m, 2H), 1.58-1.54 (m, 2H).

Workup

  1. filtrationThe reaction was filtered hot
  2. washwashed with ethanol (2×5 mL)
  3. concentrationThe filtrate was concentrated to ˜20 mL volume
  4. customresulting in the precipitation of a yellow crystalline solid
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-7a4d296d8b09415dabc2921be34f7704
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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