Acetic Acid → HCID 69562716, compound

HRID 400667Notes

Reaction equation

HRID 400667 reaction equation
[OH:1][C:2]([C:35]([F:38])([F:37])[F:36])([CH2:18][C:19]([C:22]1[C:30]2[O:29][CH2:28][CH2:27][C:26]=2[CH:25]=[C:24]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:23]=1)([CH3:21])[CH3:20])[CH2:3][C:4]#[C:5][C:6]1[C:13]([N+:14]([O-])=O)=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[CH3:17].C(O)(=O)C>C(O)C.ClCCl.[Fe]>[NH2:14][C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([CH3:17])[C:6]=1[C:5]#[C:4][CH2:3][C:2]([OH:1])([C:35]([F:37])([F:38])[F:36])[CH2:18][C:19]([C:22]1[C:30]2[O:29][CH2:28][CH2:27][C:26]=2[CH:25]=[C:24]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:23]=1)([CH3:21])[CH3:20])[C:10]#[N:11]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 60026332HCID 60026332, compound

Product 1

HCID 69562716HCID 69562716, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A stirred solution of 4-[4-hydroxy-6-(5-methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-ynyl]-3-methyl-5-nitrobenzonitrile. (165 mg, 0.3 mmol) in 6 mL of absolute ethanol was treated with 4 mL of glacial acetic acid and iron powder (335 mg, 6 mmol). The resulting mixture was heated at 90° C. for 30 minutes, cooled to room temperature, diluted with 200 mL of dichloromethane, and filtered through a pad of CELITE® filter aid. The filtrate was washed with three 50 mL portions of saturated aqueous sodium carbonate solution and two 25 mL portions of brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 140 mg of 3-amino-4-[4-hydroxy-6-(5-methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-ynyl]-5-methylbenzonitrile as a light brownish oil (90% yield).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a pad of CELITE®
  3. filtrationfilter aid
  4. washThe filtrate was washed with three 50 mL portions of saturated aqueous sodium carbonate solution and two 25 mL portions of brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fedc7ffde33349b893d6a0bca5c2032c
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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