Hydrochloric Acid → Methyl 5-amino-2,2-dimethyl-4-(methylamino)-2,3-dihydrobenzofuran-7-carboxylate

HRID 1898329Notes

Reaction equation

HRID 1898329 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[C:7]([NH:18][CH3:19])=[C:8]([N+:15]([O-])=O)[CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[O:3]1.Cl>[Fe].CO>[NH2:15][C:8]1[CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]2[O:3][C:2]([CH3:20])([CH3:1])[CH2:6][C:5]=2[C:7]=1[NH:18][CH3:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67502978Methyl 2,2-dimethyl-4-(methylamino)-5-nitro-2,3-dihydrobenzofuran-7-carboxylate

Product 1

HCID 67503505Methyl 5-amino-2,2-dimethyl-4-(methylamino)-2,3-dihydrobenzofuran-7-carboxylateYield 94.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared following the procedure described for Step-9 of Intermediate-1 using methyl 2,2-dimethyl-4-(methylamino)-5-nitro-2,3-dihydrobenzofuran-7-carboxylate (1.3 g), iron powder (cat. amt.), conc HCl (catalytic amount) and methanol (100.0 mL) to afford 1.1 g of desired product.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-904a58c5e2364c64a7b3ad3dce326531
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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