Ammonium Chloride → HCID 69448738, compound

HRID 2416208Notes

Reaction equation

HRID 2416208 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[C:6]([N+:12]([O-])=O)[CH:5]=1.[NH4+].[Cl-]>CCO.[Fe]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[C:6]([NH2:12])[CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 10943774Methyl 4-(hydroxymethyl)-3-nitrobenzoate

Product 1

HCID 69448738HCID 69448738, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-hydroxymethyl-3-nitro-benzoic acid methyl ester (step (b), 5.6 g, 26.5 mmol) in 60 mL EtOH/30 mL H2O was added Fe powder (7.5 g, 134.3 mmol) and NH4Cl (0.75 g, 14.0 mmol). The reaction mixture was stirred at 75° C. for 3 h, then filtered while hot through Celite. The Celite was washed with EtOAc and MeOH. The filtrate was concentrated in vacuo and partitioned between EtOAc/H2O. The EtOAc layers was dried over MgSO4 and concentrated in vacuo to give a yellow solid. MS m/z: 179.9 (M−1).

Workup

  1. filtrationfiltered while hot through Celite
  2. washThe Celite was washed with EtOAc and MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompartitioned between EtOAc/H2O
  5. dry with materialThe EtOAc layers was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid

Sources & evidence

ORD record
ord-9541bd7d11414f3d88b88300ebd087e1
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

Loading…