Hydrochloric Acid → HCID 24947781, compound

HRID 1803590Notes

Reaction equation

HRID 1803590 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([Cl:20])=[N:15][N:14]=[C:13]3Cl)=[O:9])[CH:2]=1.[OH-].[Na+].[O:25]1CCOCC1.Cl>O>[C:1]1([CH3:22])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([Cl:20])=[N:15][NH:14][C:13]3=[O:25])=[O:9])[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86620975HCID 86620975, compound

Product 1

HCID 24947781HCID 24947781, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1,4-dichloro-phthalazine-6-carboxylic acid m-tolylamide (350 mg, 0.87 mmol), 2N NaOH (4.4 mL, 8.70 mmol) and dioxane (4 mL) was heated to 50° C. for 3 h. The reaction was diluted with water, acidified with conc. HCl to ˜pH 6. The reaction mixture was concentrated to low volume and filtered through celite. Chromatography (Hex/EtOAc) afforded 1-chloro-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid m-tolylamide (8 mg) as a pale yellow solid, 1H NMR (400 MHz, d6-DMSO) δ: 2.32 (s, 3H), 7.96 (d, 1H), 7.26 (t, 1H), 7.60 (d, 1H), 7.65 (s, 1H), 8.14 (d, 1H), 8.52 (dd, 1H), 8.87 (s, 1H), 10.67 (s, 1H), 13.00 (bs, 1H) ppm; m/z (M−1) 312.13; and 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid m-tolylamide (23 mg) as a pale yellow solid. 1H NMR (400 MHz, d6-DMSO) δ: 2.11 (s, 3H), 6.76 (m, 1H), 7.05 (m, 1H), 7.40 (m, 2H), 8.25 (m, 3H), 10.42 (s, 1H), 12.80 (s, 1H) ppm; m/z (M−1) 312.13.

Workup

  1. concentrationThe reaction mixture was concentrated to low volume
  2. filtrationfiltered through celite

Sources & evidence

ORD record
ord-417c2fc62fd84b94a6e2f634e7ddaf2d
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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