Chloroacetaldehyde → Hydrochloric Acid

HRID 2239877Notes

Reaction equation

HRID 2239877 reaction equation
[Cl:1][CH2:2][CH:3]=O.[Br:5][C:6]1[C:11]([CH2:12][CH3:13])=[C:10]([Cl:14])[N:9]=[N:8][C:7]=1[NH2:15].CCOC1C=CC(N)=CC=1>CCO>[Br:5][C:6]1[C:7]2[N:8]([CH:2]=[CH:3][N:15]=2)[N:9]=[C:10]([Cl:14])[C:11]=1[CH2:12][CH3:13].[ClH:1]

Participants

6

Reactant 3

HCID 33ChloroacetaldehydeHCID 90764-EthoxyanilineHCID 86611752HCID 86611752, compound

Product 2

HCID 313Hydrochloric AcidYield 376.5%HCID 86611753HCID 86611753, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Chloroacetaldehyde (17.26 ml, 0.111 mol, 50% in H2O) was added to a solution of crude 4-bromo-6-chloro-5-ethylpyridazin-3-amine (5.23 g, 0.022 mol) from 1c in EtOH (30 mL). The mixture was heated in a sealed vial at 50° C. for 24 h. Solvent was removed in vacuo and the solid was resuspended in acetone/Et2O (1/1, 5 mL), filtered, and then washed with Et2O to give 8-bromo-6-chloro-7-ethylimidazo[1,2-b]pyridazine as an HCl salt (3.02 g, >80% pure). LC/MS, m/e 260 (M+1). HPLC Rt, 2.68 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. customSolvent was removed in vacuo
  2. filtrationfiltered
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-ea2ba62ef3e74b8398fe17bdd36dfa10
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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