Sodium Hydroxide → 5-(4-(4-Phenoxyphenylamino)-quinolin-7-yl)furan-2-carbaldehyde

HRID 1497609Notes

Reaction equation

HRID 1497609 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[O:26][C:27]([CH:30]5OCC[O:31]5)=[CH:28][CH:29]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>Cl.O1CCCC1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[O:26][C:27]([CH:30]=[O:31])=[CH:28][CH:29]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21952237(4-Phenoxyphenyl)-(7-(5-(1,3-dioxolan-2-yl)furan-2-yl)-quinolin-4-yl)amine

Product 1

HCID 219519195-(4-(4-Phenoxyphenylamino)-quinolin-7-yl)furan-2-carbaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

(4-Phenoxyphenyl)-(7-(5-(1,3-dioxolan-2-yl)furan-2-yl)-quinolin-4-yl)amine (1.4 g) was treated with 1M aqueous hydrochloric acid-tetrahydrofuran (60 ml, 1:1) in accordance with procedure C. Addition of 1M aqueous sodium hydroxide solution to pH 10 followed by extraction with ethyl acetate, drying (magnesium sulfate) and concentration to dryness afforded a yellow solid (1.2 g); δH [2H6] DMSO 9.70 (1H, s), 9.10 (1H, s), 8.51 (2H, m), 8.35 (1H, s), 8.02 (1H, d), 7.73 (1H, d), 7.57 (1H, d), 7.42 (4H, m), 7.22-7.04 (5H, m), 6.88 (1H, d); m/z 407 (M+1)+.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. customdrying
  3. concentration(magnesium sulfate) and concentration to dryness

Sources & evidence

ORD record
ord-8d26241ea725499da8824d912658141f
Source dataset
uspto-grants-2015_12
Patent number
US09199973B2

Reaction notes

Loading…