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

HRID 1708502Notes

Reaction equation

HRID 1708502 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:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:9][CH:8]=1)[C:4](O)=[O:5].C1C2C(=CC=CC=2)C=CC=1COC1C=C(C([O:49][N:50]=[CH:51]C(O)=O)CCCC2C=CC=CC=2)C=CC=1.N>>[OH:49][N:50]([CH3:51])[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:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 189589872-Methoxy-2-[4-(pyrid-2-ylmethoxy)phenyl]acetic acidHCID 54128871{[1-(3-[2-Naphthylmethoxy]-phenyl)4-phenylbutyl]oximino}acetic acid

Product 1

HCID 152303352-Methoxy-2-[4-(pyrid-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-(pyrid-2-ylmethoxy)phenyl]acetic acid for {[1-(3-[2-naphthylmethoxy]phenyl)-4-phenylbutyl]oximino}acetic acid. 1H NMR (DMSO-d6, 300 MHz) δ 3.07 (s, 3H), 3.12 (s, 3H), 5.18 (s, 2H), 5.23 (s, 1H), 7.0 (d, J=7Hz, 2H), 7.3 (d, J=7Hz, 2H), 7.34 (m, 1H), 7.5 (d, J=7Hz, 1H), 7.83 (dt, J=7Hz, 2Hz, 1H), 8.04 (m, 1H), 9.9 (bs, 1H). IR (CDCl3): 3620, 3500, 1640, 1610 cm-1. MS (DCI/NH3) m/e 301 (M+H)+. Analysis calcd for C16H18N2O4 ·0.5 H2O: C, 61.73; H, 6.15; N, 9.04. Found: C, 61.96; H, 5.77; N, 8.86. (In some examples O-acylated products were isolated.)

Workup

  1. custom(In some examples O-acylated products were isolated

Sources & evidence

ORD record
ord-7f1e24c0d42249b9a1ee2ff37e89afcb
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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