HCID 68107093, compound → HCID 68107386, compound

HRID 2364727Notes

Reaction equation

HRID 2364727 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:9][C:8]2=[C:10]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH:11]=[CH:12][C:13]([N+:14]([O-])=O)=[C:7]2[O:6]1)[CH3:3]>C(O)(=O)C.[Fe]>[NH2:14][C:13]1[CH:12]=[CH:11][C:10]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[C:8]2[C:7]=1[O:6][CH:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH2:9]2

Participants

4

Reactant 1

HCID 68107093HCID 68107093, compound

Product 1

HCID 68107386HCID 68107386, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Benzyl 2-(dimethylaminomethyl)-7-nitro-2,3-dihydrobenzofuran-4-carboxylate 29f (240 mg, 0.67 mmol) was dissolved in 30 mL of acetic acid followed by the addition of iron powder (189 mg, 3.37 mmol). The reaction solution was stirred for 2 hours. The resulting solution was concentrated under reduced pressure, added with 20 mL of water and 20 mL of dichloromethane, then added dropwise with 2 M sodium carbonate solution to adjust pH to about 10 and extracted with dichloromethane (30 mL×3). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound benzyl 7-amino-2-(dimethylaminomethyl)-2,3-dihydrobenzofuran-4-carboxylate 29g (212 mg, yield: 97.2%) as a yellow oil liquid.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. additionadded with 20 mL of water and 20 mL of dichloromethane
  3. additionadded dropwise with 2 M sodium carbonate solution
  4. extractionextracted with dichloromethane (30 mL×3)
  5. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-59e1909104824beea9d0d29c123b2c13
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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