Ammonia → 2-Methoxy-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid N-hydroxy-N-methyl-amide

HRID 1708498Notes

Reaction equation

HRID 1708498 reaction equation
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:9][CH:8]=1)[C:4](O)=[O:5].C1C2C(=CC=CC=2)C=CC=1COC1C=C(C([O:53][N:54]=[CH:55]C(O)=O)CCCC2C=CC=CC=2)C=CC=1.N>>[OH:53][N:54]([CH3:55])[C:4](=[O:5])[CH:3]([O:2][CH3:1])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 189589802-Methoxy-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acidHCID 54128871{[1-(3-[2-Naphthylmethoxy]-phenyl)4-phenylbutyl]oximino}acetic acid

Product 1

HCID 537551112-Methoxy-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid N-hydroxy-N-methyl-amide

Procedure

The desired material was prepared according to the procedures described in Example 5 substituting 2-methoxy-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid for {[1-(3-[2-naphthylmethoxy]phenyl)-4-phenylbutyl]oximino}acetic acid. 1H NMR (DMSO-d6, 300 MHz) δ 3.06 (s, 3H), 3.21 (s, 3H), 5.24 (s, 1H), 5.37 (s, 2H), 7.03 (d, J=7Hz, 2H), 7.3 (d, J=7Hz, 2H), 7.63 (m, 1H), 7.68 (d, J=8Hz, 1H), 7.8 (dt, J=8Hz, 2Hz, 1H), 8.0 (m, 2H), 8.42 (d, J=8Hz, 1H), 9.9 (s, 1H). IR (CDCl3): 3640, 3500, 3220, 1640, 1610 cm-1. MS (DCI/NH3) m/e 353 (M+H)+. Analysis calcd for C20H20N2O4 : C, 68.17; H, 5.72; N, 7.95. Found: C, 67.32; H, 5.61; N, 7.94.

Sources & evidence

ORD record
ord-3048ab2968cb40848626fbbcb81f95f3
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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