Sodium Hydroxide → HCID 178423897, compound

HRID 643293Notes

Reaction equation

HRID 643293 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>O.C(O)(=O)C.S(=O)(=O)(O)O>[CH3:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[N:5]=[N:1][C:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[C:13]2[OH:21]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 68579137HCID 68579137, compound

Product 1

HCID 178423897HCID 178423897, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of sodium nitrite (0.20 g, 2.8 mmol) in water (0.5 mL) was added dropwise, to a solution of 1-(2-amino-3-methylphenyl)-2-phenylethanone (0.42 g, 1.9 mmol) in acetic acid (9 mL) and sulfuric acid (1.5 mL). After the solution was stirred for 20 min at 80° C., the solution was poured into iced water. After the pH was adjusted to 6 with 2 N sodium hydroxide. The aqueous layer was extracted with ethyl acetate. The combined organics was dried over MgSO4 and concentrated. The material was purified via column chromatography using 5-50% ethyl actetate in hexane as the eluent to yield 0.10 g of 8-methyl-3-phenylcinnolin-4-ol as a gum. MS (ESI) m/z 237; HRMS (ESI, [M+H]+) 237.102;

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialThe combined organics was dried over MgSO4
  3. concentrationconcentrated
  4. customThe material was purified via column chromatography

Sources & evidence

ORD record
ord-02a69ffe2cd1431da50aa23caa305ac1
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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