Sodium Hydroxide → HCID 59011328, compound

HRID 600208Notes

Reaction equation

HRID 600208 reaction equation
[N:1]([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:10]=[CH:9][C:7]=1[NH2:8].O.O.[Sn](Cl)Cl.[OH-].[Na+]>O.Cl.ClCCl>[F:5][C:6]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:10]=[CH:9][C:7]=1[NH:8][NH2:1]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 23668193Sodium NitriteHCID 58307317HCID 58307317, compound

Product 1

HCID 59011328HCID 59011328, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of sodium nitrite (0.38 g, 5.4 mmol) in 20 mL water is slowly added dropwise at −15° C. to a solution of 2-fluoro-4-(2-morpholin-4-yl-ethoxy)aniline (1.7 g, 4.5 mmol) in 20 mL conc. hydrochloric acid. The resulting suspension is stirred for 4 h at −10° C., before a solution of tin(II)chloride dihydrate (2.6 g, 11.3 mmol) in 20 mL conc. hydrochloric acid is added dropwise. After 14 h stirring at RT the reaction mixture is adjusted to pH 10 with 10 N NaOH and combined with dichloromethane. After filtration through Celite® the filtrate is extracted with dichloromethane. The combined organic phases are dried on magnesium sulphate and evaporated down in vacuo. Yield: 1.5 g.

Workup

  1. additionis added dropwise
  2. filtrationAfter filtration through Celite® the filtrate
  3. extractionis extracted with dichloromethane
  4. customThe combined organic phases are dried on magnesium sulphate
  5. customevaporated down in vacuo

Sources & evidence

ORD record
ord-b1b57c78535c4e55b114df0f7649a3f5
Source dataset
uspto-grants-2011_03
Patent number
US07902183B2

Reaction notes

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