HCID 883681, compound → HCID 16775977, compound

HRID 1514811Notes

Reaction equation

HRID 1514811 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1.[H][H]>CCO.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:17])=[O:16]

Participants

5

Reactant 2

HCID 883681HCID 883681, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 16775977HCID 16775977, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(2-dimethylaminoethyl)-3-nitrobenzamide (21.0 g, 88.0 mmol) in EtOH (50 mL) was added 10% Pd/C (2.52 g) and the hydrogenated with hydrogen at 35 psi for 3 h. The reaction mixture was filtered through a pad of Celite, the filterate was evaporated to dryness and the solid obtained was recrystallize from EtOH to give 3-amino-N-(2-dimethylaminoethyl)benzamide; 17.19 g (93%); mp 97-100° C.; 1H NMR (CDCl3) δ 2.20 (6H, s, 2×Me), 2.52 (2H, J=5.8 Hz, CH2), 3.51 (2H, q, J=5.4 and 5.8 Hz, CH2), 3.80 (2H, brs, exchangeable, NH2), 6.75-6.80 (1H, m, ArH), 6.82 (1H, brs, exchangeable, NH), 7.10 (H, d, J=7.6 Hz, ArH) 7.12-7.30 (2H, m, ArH) 8.33 (1H, m, ArH), 8.66 (1H, s, ArH). Anal Calcd. for (C11H17N3O): C, 63.74; H, 8.27; N 20.27. Found: C, 63.51, H, 8.45; N 20.12.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. customthe filterate was evaporated to dryness
  3. customthe solid obtained
  4. customwas recrystallize from EtOH

Sources & evidence

ORD record
ord-1c63b885e95f40deaf111c215e247ddb
Source dataset
uspto-grants-2012_07
Patent number
US08222297B2

Reaction notes

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