HCID 66876546, compound → HCID 66876719, compound

HRID 871283Notes

Reaction equation

HRID 871283 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([O:18][CH3:19])=[CH:7][C:8]([N+:15]([O-])=O)=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11]>[Pd].CCOC(C)=O.CO>[NH2:15][C:8]1[CH:7]=[C:6]([O:18][CH3:19])[C:5]([O:4][CH2:3][CH2:2][Cl:1])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 1

HCID 66876546HCID 66876546, compound

Product 1

HCID 66876719HCID 66876719, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To methyl 5-(2-chloroethoxy)-4-methoxy-2-nitrobenzoate (4.07 g, 14.1 mmol) under argon was added 10% palladium on carbon and in EtOAc (150 mL) and MeOH (50 mL). The flask was flushed with H2 (g) and stirred under H2 (1 atm) for 30 minutes. The mixture was filtered through Celite and concentrated in vacuo to give methyl 2-amino-5-(2-chloroethoxy)-4-methoxybenzoate (3.61 g, 13.9 mmol, 99%). 1H NMR (300 MHz, DMSO-d6) δ 7.20 (s, 1H), 6.52 (br s, 2H), 6.38 (s, 1H), 4.07 (t, 2H), 3.85 (t, 2H), 3.77 (s, 3H), 3.75 (s, 3H); LC-MS (ESI) m/z 260 (M+H)+.

Workup

  1. customThe flask was flushed with H2 (g)
  2. filtrationThe mixture was filtered through Celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d022251cf75492faca3e2f6dd585ce8
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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