HCID 67255056, compound → HCID 67254489, compound

HRID 1830738Notes

Reaction equation

HRID 1830738 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:5]=1>CO.[Cl-].[NH4+].C(OCC)(=O)C.[Zn]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])[CH:5]=1

Participants

6

Reactant 1

HCID 67255056HCID 67255056, compound

Product 1

HCID 67254489HCID 67254489, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred, cooled (about 0° C.) solution of 3-(3-dimethylamino-propoxy)-4-nitro-benzoic acid methyl ester (282 mg, 1.0 mmol) in methanol (2 mL) and saturated aqueous ammonium chloride (1 mL) was added zinc dust (2.0 mmol). After stirring for 12 hours, the reaction was diluted with 30 mL of ethyl acetate and washed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced pressure to yield the desired product as a tan solid (88% yield). 1H-NMR (400 MHz, CDCl3) δ7.52 (d, 1H), 7.48 (s, 1H), 7.25 (s, 1H), 6.65 (d, 1H), 4.29 (br s, 1H), 4.09 (t, 2H), 3.85 (s, 3H), 2.49 (t, 2H), 2.25 (s, 6H), 2.00 (m, 2H).

Workup

  1. washwashed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac9c7890166942aeb73d67ac0581020d
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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