Hydrochloric Acid → HCID 59385196, compound

HRID 2356825Notes

Reaction equation

HRID 2356825 reaction equation
[CH3:1][N:2]([C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11])[C:3]([CH3:9])([C:5]([O:7][CH3:8])=[O:6])[CH3:4].Cl>C(O)C.[Fe]>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:10]([N:2]([CH3:1])[C:3]([CH3:4])([C:5]([O:7][CH3:8])=[O:6])[CH3:9])=[O:11])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59385197HCID 59385197, compound

Product 1

HCID 59385196HCID 59385196, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

As shown in Reaction Scheme 11, to a solution of methyl N,2-dimethyl-N-[(4′-nitrobiphenyl-4-yl)carbonyl]alaninate (1.92 g, 5.4 mmol) in 85% ethanol (50 mL) was added iron powder (3.01 g, 53.88 mmol) and 2 M aqueous HCl solution (2.69 mL, 5.4 mmol). The resulting mixture was heated at reflux for 2.5 h. The mixture was filtered through a pad of Celite® and concentrated under reduced pressure to afford methyl N-[(4′-aminobiphenyl-4-yl)carbonyl]-N,2-dimethylalaninate as a yellow solid (1.44 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ 1.42 (s, 6H), 2.94 (s, 3H), 3.57 (s, 3H), 5.30 (broad s, 2H), 6.61 (d, 2H), 7.31-7.40 (m, 4H), 7.58 (d, 2H); LC-MS m/z 327.2 (MH+), retention time 1.84 minutes.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2.5 h
  3. filtrationThe mixture was filtered through a pad of Celite®
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae7b68a158e9408badfd981794673132
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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