Sodium Hydroxide → HCID 178426116, compound

HRID 892174Notes

Reaction equation

HRID 892174 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[Cl:7][C:8]1[CH:17]=[C:16]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)[CH:21]=2)[C:11]([O:12][CH2:13][C:14]#[N:15])=[C:10]([CH3:38])[CH:9]=1.[OH-].[Na+]>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH3:38])[C:11]([O:12][CH2:13][C:14]2[NH:15][N:3]=[N:2][N:1]=2)=[C:16]([CH:17]=1)[CH2:18][O:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22241376HCID 22241376, compound

Product 1

HCID 178426116HCID 178426116, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Sodium azide (395 mg, 6.1 mmol) and ammonium chloride (325 mg, 6.1 mmol) are added to a solution of {4-chloro-2-methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-phenoxy}-acetonitrile (300 mg, 0.68 mmol, example 36c) in DMF (2 mL) and heated at 110° C. for 2 h. The reaction is then cooled and poured into a 1 N sodium hydroxide solution (20 mL) with the formation of a solid. This mixture is then washed with ether (4×) and the ether is discarded. The remaining aqueous solution contains a solid which is filtered. This solid is dissolved in 10% ethanol water (250 mL) and the pH is lowered to about 5 with 2N HCl. A solid precipitates which is filtered to provide the title compound. m.p. 181–184° C.; 1H NMR (300 MHz, DMSO-d6) d 8.40 (d, 1H), 8.01–7.97 (m, 2H), 7.77 (dd, 1H), 7.66–7.60 (m, 2H), 7.33 (d, 2H), 7.18 (dd, 1H), 6.72 (dd, 1H), 6.65 (dd, 1H), 6.59 (dd, 1H), 5.33 (s, 2H), 5.27 (s, 2H), 5.07 (s, 2H), 2.24 (s, 3H); MS (EST) 488, 490 (M+H;Cl)+.

Workup

  1. temperatureThe reaction is then cooled
  2. washThis mixture is then washed with ether (4×)
  3. filtrationis filtered
  4. dissolutionThis solid is dissolved in 10% ethanol water (250 mL)
  5. customA solid precipitates which
  6. filtrationis filtered

Sources & evidence

ORD record
ord-8f14664698ab48ad998b1ae78dbe4441
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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