Hydrochloric Acid → HCID 44608550, compound

HRID 1943715Notes

Reaction equation

HRID 1943715 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[C:26]3[CH:25]=[N:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]=3[O:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.[Br-].[Li+].N1CCNCC1.Cl>CN(C)C=O.O>[Br:10][C:6]1[CH:5]=[C:4]([C:11]([N:13]2[C:26]3[CH:25]=[N:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]=3[O:16][CH2:15][CH2:14]2)=[O:12])[CH:3]=[C:2]([Br:1])[C:7]=1[OH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 82050Lithium BromideHCID 66936677HCID 66936677, compound

Product 1

HCID 44608550HCID 44608550, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 10 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(2,3-dihydro-4-oxa-1,9-diaza-phenanthren-1-yl)-methanone (30 mg, 0.063 mmol), lithium bromide (12 mg, 0.134 mmol) and piperazine (9 mg, 0.101 mmol) were dissolved in N,N-dimethyl formamide (3 ml), and then stirred at 100□ for 2 hours. After completion of the reaction by adding water dropwise, the mixture was adjusted to weak acidic condition (pH=6) by using 1N hydrochloric acid. The formed solid was filtered and washed with distilled water, and recrystallized from tetrahydrofuran and methanol to obtain the target compound 55, i.e., (3,5-dibromo-4-hydroxy-phenyl)-(2,3-dihydro-4-oxa-1,9-diaza-phenanthren-1-yl)-methanone, as yellow solid (10 mg, 34%).

Workup

  1. customAfter completion of the reaction
  2. filtrationThe formed solid was filtered
  3. washwashed with distilled water
  4. customrecrystallized from tetrahydrofuran and methanol

Sources & evidence

ORD record
ord-1176d247469d44a9a2ca3f1ef871af1a
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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