Water → 7-Chloroacetamido-2-methylquinoline-5,8-dione

HRID 1278593

Reaction equation

HRID 1278593 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].ClCC(N[C:17]1[CH:26]=[C:25]([NH:27][C:28](=[O:31])[CH2:29][Cl:30])[C:24]([OH:32])=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH3:33])=[N:22]2)=O.[OH2:34]>C(O)(=O)C>[Cl:30][CH2:29][C:28]([NH:27][C:25]1[C:24](=[O:32])[C:23]2[N:22]=[C:21]([CH3:33])[CH:20]=[CH:19][C:18]=2[C:17](=[O:34])[CH:26]=1)=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 24502Potassium Dichromate2×HCID 115374375,7-Bis(chloroacetamido)-8-hydroxy-2-methylquinoline

Product 1

HCID 117016887-Chloroacetamido-2-methylquinoline-5,8-dioneYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

This compound was prepared by the oxidation of the corresponding acylamido with potassium dichromate in glacial acetic acid. In a 500 ml. round-bottom flask equipped with a magnetic bar, 5,7-bis(chloroacetamido)-8-hydroxy-2-methylquinoline (32) (prepared as described in Example 32) (3.42 g., 0.01 mol) was suspended in 122 ml. of glacial acetic acid. A solution of potassium dichromate (8.8 g., 0.03 mol) in 115 ml. of water was added and the resulting dark solution was stirred at room temperature overnight. The solution was extracted with dichloromethane (12×50 ml.). The organic extracts were washed with 3% sodium bicarbonate solution (200 ml.), dried with magnesium sulfate, and rotoevaporated to yield a bright yellow solid. After vacuum drying, the nearly pure product weighed 1.56 g. (yield of 59%). The product was recrystallized from ethyl acetate: mp 196-200 EC (dec.); 1H NMR (CDCl3)*2.76 (3H, s, C—2CH3), 4.23 (2H, s, C—7NHCOCH2Cl), 7.56 (1H, d, J=8.1 Hz, C—3H), 7.89 (1H, s, C—6H), 8.30 (1H, d, J=8.1 Hz, C—4H), 9.48 (1H, br. s, C—7NH); IR (KBr) vmax 3299, 3078, 2948, 1712, 1683, 1641, 1614, 1588, 1515, 1398, 1384, 1323, 1130 cm−1; EIMS, m/e (relative intensity) 264/266 (M+, 2.9/1, 67) 229 (62), 215 (74), 201 (43), 188 (86), 161 (base), 132 (21); HRMS, m/e for C14H9ClN2O3, calculated 264.030170, found 264.029824; analysis for C14H9ClN2O3 calculated: C, 54.46; H, 3.43; Cl, 13.40; N, 10.58; found: C, 54.19; H, 3.37; Cl, 13.29; N, 10.36.

Workup

  1. customround-bottom flask equipped with a magnetic bar
  2. extractionThe solution was extracted with dichloromethane (12×50 ml.)
  3. washThe organic extracts were washed with 3% sodium bicarbonate solution (200 ml.)
  4. dry with materialdried with magnesium sulfate
  5. customto yield a bright yellow solid
  6. customAfter vacuum drying
  7. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2e9b57bc06b44b018150a53d150b6887
Source dataset
uspto-grants-2002_09
Patent number
US06444684B1

Linked notes

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