Sodium Hydroxide → HCID 117601845, compound

HRID 1773742Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([N+:19]([O-])=O)[C:10]([NH:17][CH3:18])=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])=[C:5]([CH3:22])[O:4][N:3]=1.[OH-].[Na+]>C(O)C>[NH2:19][C:9]1[C:10]([NH:17][CH3:18])=[C:11]([CH:16]=[C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:22])[CH:8]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 120 °C

Procedure

To methyl 5-(3,5-dimethylisoxazol-4-yl)-2-(methylamino)-3-nitrobenzoate (2000 mg, 6.55 mmol) was added stannous chloride (3726.66 mg, 19.65 mmol) and Ethanol (100 ml) in a pressure tube. The suspension was then heated in sealed vessel to 120° C. for 90 minutes at which point the reaction was cooled then stirred in a mixture of EtAc/1N NaOH for 1 hour or until precipitates form. Precipitates were filtered and crude mixture was diluted in EtAc and water and extracted 3× with EtAc. Organics were washed with water then brine, dried over sodium sulfate and evaporated to dryness under reduced pressure. Residue was purified by silica gel chromatography using MeOH/DCM as the eluent to afford methyl 3-amino-5-(3,5-dimethylisoxazol-4-yl)-2-(methylamino)benzoate as a dark form (1.1 g, 61%)

Workup

temperaturewas cooled
customuntil precipitates
customform
customPrecipitates
filtrationwere filtered
additioncrude mixture was diluted in EtAc and water
extractionextracted 3× with EtAc
washOrganics were washed with water
dry with materialbrine, dried over sodium sulfate
customevaporated to dryness under reduced pressure
customResidue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-285e4d8132864af38a67cd3c6575bd1e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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