Hydrochloric Acid → HCID 178518940, compound

HRID 593693Notes

Reaction equation

HRID 593693 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7](OC)=[O:8])[C:2]=1[C:11](OC)=[O:12].O.[NH2:22][NH2:23].Cl>>[C:15]1([C:1]2[CH:6]=[CH:5][CH:4]=[C:3]3[C:2]=2[C:11]([OH:12])=[N:22][N:23]=[C:7]3[OH:8])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 22341661Dimethyl 2,3-biphenyldicarboxylate

Product 1

HCID 178518940HCID 178518940, compoundYield 85.1%

Procedure

A solution of dimethyl [1,1′-biphenyl]-2,3-dicarboxylate (0.600 g, 2.22 mmol) in hydrazine hydrate (5.00 mL, 159 mmol) was heated in a sealed tube at 100° C. for 16 h. The reaction mixture was acidified to pH˜3 with 1.5N HCl. The resulting precipitate was filtered, washed with water (3×50 mL) and hexanes (2×50 mL). The precipitate was dried under vacuum to yield 5-phenylphthalazine-1,4-diol (0.450 g, 85.0%) as an off-white solid. LCMS (Condition 11): retention time 0.76 min, [M+1]=239.4. 1H NMR (400 MHz, DMSO-d6) δ 7.29-7.34 (m, 5 H), 7.60 (d, J=7.6 Hz, 1 H), 7.89 (t, J=7.6 Hz, 1 H), 8.13 (br s, 1 H), 11.40 (br s, 2 H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water (3×50 mL) and hexanes (2×50 mL)
  3. customThe precipitate was dried under vacuum

Sources & evidence

ORD record
ord-dc7a6ecdd501494f9a84506686b94389
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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