Hydrochloric Acid → HCID 22716423, compound

HRID 1582877Notes

Reaction equation

HRID 1582877 reaction equation
N[C:2]1[CH:7]=[C:6](OC)[CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([O:20][CH3:21])[C:14]([O:22][CH3:23])=[CH:13]2.Cl.[N:25]([O-:27])=[O:26].[Na+].O>C(O)(=O)C>[N+:25]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([O:20][CH3:21])[C:14]([O:22][CH3:23])=[CH:13]2)([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 22716433HCID 22716433, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22716423HCID 22716423, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-(2-Amino-4-methoxyphenyl)-2,3-dimethoxynaphthalene (32) (12 mg, 0.039 mmol) was dissolved in acetic acid (0.6 mL) and concentrated hydrochloric acid (0.06 mL). The solution was cooled in an ice bath and diazotized by the dropwise addition of a solution of sodium nitrite (0.026 g in 0.5 mL water). The resulting diazonium solution was allowed to rise to room temperature slowly and left overnight. To the resulting red solution which contained some precipitate was added 30 mL water and the mixture was extracted with ethyl acetate (30 mL×3). The organic layers were combined and washed with diluted sodium hydroxide solution first, then with water and brine. The ethyl acetate extracts were dried with anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography on silica gel using 40:60 hexanes:ethyl acetate to give the pure 4 (5 mg) in 40% yield; mp 244-246° C.; IR (KBr) 2919, 1619, 1507, 1388, 1292, 1277, 1204 cm−1; UV (MeOH) 292, 266, 216 nm; 1H NMR (CDCl3) δ4.10 (6H, s), 4.22 (3H, s), 7.32 (1H, s), 7.54 (1H, dd, J1=9.1, J2=2.6), 8.04-8.08 (2H, m), 8.28 (1H, d, J=8.9), 8.49 (1H, d, J=9.1), 9.16 (1H, s); 13C NMR δ56.33, 56.52, 56.92, 104.36, 107.93, 108.92, 116.88, 117.08, 119.48, 123.51, 124.54, 127.14, 128.42, 132.46, 141.77, 148.52, 151.12, 151.40, 160.45; HRMS (EI) calcd for C19H16N2O3 m/z: 320.1161; found: 320.0384.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customto rise to room temperature
  3. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  4. washwashed with diluted sodium hydroxide solution first
  5. dry with materialThe ethyl acetate extracts were dried with anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel using 40:60 hexanes

Sources & evidence

ORD record
ord-721300e38ef349a584f1f08f84b6297a
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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