Sodium Hydroxide → 4-[3-[(E)-(1-benzylindol-2-yl)methylideneamino]oxypropoxy]-2-hydroxybenzoic acid

HRID 1392279Notes

Reaction equation

HRID 1392279 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:16]/[C:17]2[N:18]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:6][C:5]=1[OH:33].[OH-].[Na+]>>[CH2:26]([N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[C:17]1/[CH:16]=[N:15]/[O:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:34])=[O:2])=[C:5]([OH:33])[CH:6]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 87729992methyl 4-[3-[(E)-(1-benzylindol-2-yl)methylideneamino]oxypropoxy]-2-hydroxybenzoate

Product 1

HCID 115323534-[3-[(E)-(1-benzylindol-2-yl)methylideneamino]oxypropoxy]-2-hydroxybenzoic acidYield 62%

Procedure

This compound was produced using similar methods as those used in Step 5, example 3, starting with 4-[3-({[(1E)-(1-benzyl-1H-indol-2-yl)methylidene]amino}oxy)propoxy]-2-hydroxybenzoic acid methyl ester (0.104 g, 0.23 mmol) and 2.5 M sodium hydroxide solution (3 mL). The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (10/90 with 1% formic acid gradient to 20/80 with 1% formic acid) followed by recrystallization one time from methylene chloride/hexanes to give 4-[3-({[(1E)-(1-benzyl-1H-indol-2-yl)methylidene]amino}oxy)propoxy]-2-hydroxybenzoic acid (0.063 g, 62%) as a white solid. mp=175-176° C. (dec). 1H NMR (400 MHz, DMSO-d6); δ 11.50 (bs, 1H), 8.41 (s, 1H), 7.68 (d, 1H), 7.60 (d, 1H), 7.48 (d, 1H), 7.25-7.16 (m, 5H), 7.06 (t, 1H), 6.99 (d, 2H), 6.91 (s, 1H), 6.47 (d, 1H), 6.44 (s, 1H), 5.75 (s, 2H), 4.18 (t, 2H), 4.05 (t, 2H), 2.00 (m, 2H). Mass spec; (ES+) m/z 445.1, (ES−) m/z 443.4. Elemental analysis; Calculated for C26H24N2O5: C, 70.26; H, 5.44; N, 6.30. Found: C, 69.86; H, 5.43; N, 6.09.

Workup

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel
  3. customfollowed by recrystallization one time from methylene chloride/hexanes

Sources & evidence

ORD record
ord-c7d9c0a431c144da875fe810702dfd85
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

Loading…