Ammonium Chloride → Methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoate

HRID 2208720Notes

Reaction equation

[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[C:9]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate (5.6 g, 20.97 mmol) in ethanol (40 mL) was added ammonium chloride (5.6 g, 104.6 mmol) dissolved in water (30 mL) and iron powder (4.67 g, 85.16 mmol). The resulting mixture was heated at 80° C. for 1 h. On completion, water was added to the reaction then the mixture was filtered through celite. The filtrate was extracted with ethyl acetate. The combined organic layers were dried then concentrated under reduced pressure to give methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoate.

Workup

filtrationthe mixture was filtered through celite
extractionThe filtrate was extracted with ethyl acetate
customThe combined organic layers were dried
concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record: ord-af9bf1f0c6f041aeba98c2dd17c1c443
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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