Hydrochloric Acid → HCID 22997642, compound

HRID 1166222Notes

Reaction equation

HRID 1166222 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH2:12][CH:13]=[CH2:14])[C:6]=1[O:15][CH3:16])([O-])=O.[Sn].[OH-].[Na+]>>[NH2:2][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH2:12][CH:13]=[CH2:14])[C:6]=1[O:15][CH3:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 22997663HCID 22997663, compound

Product 1

HCID 22997642HCID 22997642, compoundYield 95.6%

Conditions

Temperature
0 °C

Procedure

Concentrated HCl (25 ml) was added to a mixture of 2-nitro-4-chloro-6-allylanisole (11.25 g) and granulated tin (9.02 g). The resulting mixture was stirred for 1 hour with heating at a boiling water bath temperature. The reaction mixture was then cooled to 0° C. and was made basic by addition of 10 N NaOH. The resulting mixture was extracted with dichloromethane. The organic layer was washed with water, dried over MgSO4, and concentrated in vacuo to give crude 2-amino-4-chloro-6-allylanisole (9.34 g, 95%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ6.61 (d, J=2.5 Hz, 1 H), 6.55 (d, J=2.5 Hz, 1 H), 5.98-5.89 (m, 1 H), 5.13-5.06 (m, 2 H), 3.72 (s, 3 H), 3.36 (d, J=6.5 Hz, 2 H).

Workup

  1. temperaturewith heating at a boiling water bath temperature
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-134965a0c448408db64e19746dbda3b3
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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