Hydrochloric Acid → 7-Amino-6-chloro-2-methylquinoline-5,8-dione

HRID 1278595

Reaction equation

HRID 1278595 reaction equation
[ClH:1].C([NH:5][C:6]1[C:15](=[O:16])[C:14]2[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10][C:9]=2[C:8](=[O:18])[CH:7]=1)(=O)C.C(=O)(O)[O-].[Na+]>CO>[NH2:5][C:6]1[C:15](=[O:16])[C:14]2[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10][C:9]=2[C:8](=[O:18])[C:7]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 98345267-Acetamido-2-methylquinoline-5,8-dione

Product 1

HCID 105610247-Amino-6-chloro-2-methylquinoline-5,8-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slow stream of hydrogen chloride gas was passed through a solution of 7-acetamido-2-methylquinoline-5,8-dione (6, 230 mg, 1 mmol) in dry methanol (15 ml)at 60° C. for 48 h. (See Equation 11 below) The resulting acidic solution was neutralized with 2% sodium bicarbonate (10 ml), extracted with CH2Cl2 (5×30 ml) and dried over sodium sulfate (2.0 g, 20 min). Evaporation of the solvent in vacuo afforded 98 mg (42%) of pure (59) as red crystals: mp 270° C. (Dec.,MeOH); 1H NMR (CDCl3) δ8.31 (1H, d, J=8.0 Hz, H—4), 7.47 (1H, d, J=8.0 Hz, H—3), 5.70 (2H, br s, NH2), 2.68 (3H, s, CH3); IR (KBr) Vmax 3471, 3329, 3191, 3085, 2960, 2924, 1649, 1605, 1587, 1573, 1382, 1370, 1326, 1273, 1259, 1164, 737 cm−1; EIMS, m/e (relative intensity) 223 (M+1, 100), 189 (4.1), 133 (0.4), 81 (0.8), 69 (1.2); EIMS, m/e (relative intensity) 224 (M+2, 27.3), 222 (M+, 97.2), 195 (7.4), 187 (M−Cl, 100), 166 (5.3), 131 (10.4), 104 (12.1), 77 (14.9), 64 (10.5); HRMS, m/e for C10H7CIN2O2 calcd 222.0196, found 222.0194.

Workup

  1. extractionextracted with CH2Cl2 (5×30 ml)
  2. dry with materialdried over sodium sulfate (2.0 g, 20 min)
  3. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-b538e9e9303e477d8daa909bca16bd51
Source dataset
uspto-grants-2002_09
Patent number
US06444684B1

Linked notes

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