Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86598745, compound

HRID 2104486Notes

Reaction equation

[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([OH:23])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.[CH3:58][NH:59][O:60][CH3:61].C(N(C(C)C)CC)(C)C>O.CN(C=O)C>[CH3:61][O:60][N:59]([CH3:58])[C:21]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Phenyl-8-(trifluoromethyl)quinoline-3-carboxylic acid (6.19 g, 19.51 mmol) was taken into DMF (75 mL) and cooled to 0° C. Then PyBOP (10.66 g, 20.49 mmol) was added followed by N,O-dimethylhydroxylamine hydrochloride (2.09 g, 21.46 mmol) and diisopropylethylamine (8.50 mL, 48.78 mmol). The reaction was stirred for 3 hours allowing to warm to room temperature during that time. The reaction was poured into water and extracted with ethyl acetate. The combined organics was washed with water, half-saturated brine and then dried over magnesium sulfate. Purification was carried out via column chromatography using 30% ethyl acetate in hexane as the eluent to yield the desired compound as a white solid (6.37 g, 90.6%). MS (ESI) m/z 361 ([M+H]+); Anal. Calcd for C19H15F3N2O2.0.15H2O: C, 62.86; H, 4.25; N, 7.72. Found: C, 62.89; H, 4.14; N, 7.55.

Workup

temperatureto warm to room temperature during that time
extractionextracted with ethyl acetate
washThe combined organics was washed with water, half-saturated brine
dry with materialdried over magnesium sulfate
customPurification

Sources & evidence

ORD record: ord-bbc44edba67543e29c41eb226b7e214b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576215B2

Reaction notes

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