Hydrogen Bromide → HCID 136131615, compound

HRID 911204Notes

Reaction equation

HRID 911204 reaction equation
Br.[CH2:2]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[N:6][C:5]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=1)[CH3:3].C([O-])([O-])=O.[Na+].[Na+]>CC(O)=O>[CH2:2]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[N:6][C:5]=1[NH:16][C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)[CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 57756259HCID 57756259, compound

Product 1

HCID 136131615HCID 136131615, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

A RBF was charged with 13.9 mL of 1:1 AcOH:HBr and 4-ethyl-N-(4-methoxyphenyl)-6-phenylpyridazin-3-amine (1.27 g, 4.16 mmol). The flask was fitted with a reflux condenser and was heated at 140° C. for 4 h. Upon cooling, the reaction mixture was poured into ice water and brought to neutral pH by careful addition of 2M aqueous Na2CO3. The resulting precipitate was filtered, washed with water and dried under vacuum to provide 4-(4-ethyl-6-phenylpyridazin-3-ylamino)phenol as a tan solid. MS m/z=292 [M+H]+. Calc'd for C18H17N3O: 291.35.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperatureUpon cooling
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e0f90fa98a1f4748b34226e0a1279699
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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