HCID 66891597, compound → HCID 66889618, compound

HRID 2369920Notes

Reaction equation

HRID 2369920 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH2:4][NH:5][C:6]1[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[H][H]>C(O)C.[Pd]>[NH2:16][C:15]1[C:6]([NH:5][CH2:4][CH:3]([O:19][CH3:20])[O:2][CH3:1])=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 66891597HCID 66891597, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66889618HCID 66889618, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an argon purged solution of methyl 2-(2,2-dimethoxyethylamino)-3-nitrobenzoate (1.4 g, 4.7 mmol) from Step B above in ethanol (50 mL) at room temperature was added 10% palladium on carbon. A hydrogen balloon was then attached and the suspension was stirred overnight at room temperature. The reaction mixture was filtered through celite and concentrated under reduced pressure to give methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (1.2 g, quantitative yield) as a dark red oil: 1H NMR (300 MHz, DMSO-d6) δ 7.06 (d, J=5.0 Hz, 1H), 6.85 (dd, J=7.8, 1.2 Hz, 1H), 6.74 (t, J=7.8 Hz, 1H), 6.06 (t, J=7.5 Hz, 1H), 4.84 (s, 2H), 4.38 (t, J=5.4 Hz, 1H), 3.80 (s, 3H), 3.23 (s, 6H), 3.04 (dd, J=7.2, 5.7 Hz, 2H); MS (ESI+) m/z 254 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29ddad9c33404947a8f25c0160e87e35
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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