Hydrochloric Acid → HCID 90410881, compound

HRID 717374Notes

Reaction equation

HRID 717374 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[NH4+].[Cl-].Cl>[Fe].O>[NH2:19][C:18]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 25517Ammonium ChlorideHCID 77230410HCID 77230410, compound

Product 1

HCID 90410881HCID 90410881, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Into a 500-mL 4-necked round-bottom flask, was placed methyl 2-(benzyloxy)-3-nitrobenzoate (20 g, 69.62 mmol, 1.00 equiv), ethanol (200 mL), water (100 mL) and NH4Cl (11.1 g, 207.52 mmol, 2.98 equiv). This was followed by the addition of Fe (19.5 g) in portions. To the mixture was added hydrogen chloride (5 mL). The resulting solution was stirred for 5 h at 85° C. in an oil bath. The solids were filtered out. The filter cake was washed with 3×50 mL of ethanol. The resulting mixture was concentrated under vacuum. The residue was dissolved in 1000 mL of ethyl acetate. The resulting mixture was washed with 3×800 mL of water. The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 17 g (95%) of methyl 3-amino-2-(benzyloxy)benzoate as yellow oil. MS (ESI) m/z 258 ([M+H]+).

Workup

  1. customInto a 500-mL 4-necked round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. washThe filter cake was washed with 3×50 mL of ethanol
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. dissolutionThe residue was dissolved in 1000 mL of ethyl acetate
  6. washThe resulting mixture was washed with 3×800 mL of water
  7. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 17 g (95%) of methyl 3-amino-2-(benzyloxy)benzoate as yellow oil

Sources & evidence

ORD record
ord-2ad72ccd35ea45dc8a2eb7d31d84eaf4
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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