Hydrogen Bromide → HCID 12231775, compound

HRID 1042834Notes

Reaction equation

HRID 1042834 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9][N:8]=1.Br.O>C(O)(=O)C>[C:17]1([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([NH2:6])=[N:8][N:9]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 67317949HCID 67317949, compound

Product 1

HCID 12231775HCID 12231775, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

In a 150 mL sealed tube, dissolved N-(2,4-dimethoxybenzyl)-4-phenylphthalazin-1-amine (3.00 g, 8.1 mmol) in acetic acid (40 mL). Hydrobromic acid (48% aqueous) (2.6 mL, 24 mmol) was added and the tube was stirred at 90° C. for 3 h. The solution was cooled to RT, and slowly poured into water, which caused a pink solid to crash out. The solid was filtered and rinsed with water. The product containing filtrate was slowly poured into saturated sodium carbonate. The aqueous phase was extracted with DCM, washed twice with water, dried with Na2SO4, filtered through flitted funnel, and concentrated to yield 4-phenylphthalazin-1-amine as light yellow solid. MS [M+H]=222; Calc'd 221.3 for C14H11N3.

Workup

  1. customIn a 150 mL sealed tube
  2. temperatureThe solution was cooled to RT
  3. filtrationThe solid was filtered
  4. washrinsed with water
  5. additionThe product containing filtrate
  6. additionwas slowly poured into saturated sodium carbonate
  7. extractionThe aqueous phase was extracted with DCM
  8. washwashed twice with water
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered through flitted funnel
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d789706e46ba4e26931e21c8adea8997
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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