Sodium Hydroxide → HCID 58976138, compound

HRID 1179223Notes

Reaction equation

HRID 1179223 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[F:8][CH:9]([F:24])[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=1[O:20][CH:21]([CH3:23])[CH3:22].[OH-].[Na+]>Cl.C(OCC)(=O)C>[F:8][CH:9]([F:24])[O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[O:20][CH:21]([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 58976196HCID 58976196, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 58976138HCID 58976138, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To tin chloride dihydrate (5.46 g, 24.2 mmol) in concentrated HCl (7 mL) at 0° C. was added 1-difluoromethoxy-2-isopropoxy-4-nitro-benzene (1.712 g, 6.92 mmol) in ethyl acetate (7 mL) and the reaction was stirred for 1 h. The reaction was adjusted to ˜pH7 with NaOH and was filtered through Celite, washing with ethyl acetate. The filtrate was separated and the aqueous phase was back extracted with ethyl acetate. The combined organic phase was washed with brine, dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 2:8 ethyl acetate:hexanes provided 4-difluoromethoxy-3-isopropoxy-phenylamine (0.55 g, 37% yield, 57% yield based on recovered starting material) as an orange oil. 1H-NMR (CDCl3, 500 MHz) 6.94 (d, 1H), 6.41 (t, 1H), 6.31 (dd, 1H), 6.23 (d, 1H), 4.47 (m, 1H), 1.33 (d, 6H) ppm; MS (FIA) 218.2 (M+H); HPLC (Method A) 2.853 min.

Workup

  1. filtrationwas filtered through Celite
  2. washwashing with ethyl acetate
  3. customThe filtrate was separated
  4. extractionthe aqueous phase was back extracted with ethyl acetate
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. customevaporated
  8. customPurification by flash chromatography (SiO2)
  9. washeluted with 2:8 ethyl acetate

Sources & evidence

ORD record
ord-623f55c894d0469eaf019d2babe6c652
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

Loading…