Diethylcarbamoyl chloride → HCID 14626124, compound

HRID 1638703Notes

Reaction equation

HRID 1638703 reaction equation
[OH:1][C:2]1[N:3]=[C:4]([CH3:19])[C:5]2[C:10]([C:11]=1[N+:12]([O-:14])=[O:13])=[CH:9][C:8]([O:15][CH3:16])=[C:7]([O:17][CH3:18])[CH:6]=2.C(N(CC)CC)C.[CH2:27]([N:29]([CH2:33][CH3:34])[C:30](Cl)=[O:31])[CH3:28]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:27]([N:29]([CH2:33][CH3:34])[C:30]([O:1][C:2]1[N:3]=[C:4]([CH3:19])[C:5]2[C:10]([C:11]=1[N+:12]([O-:14])=[O:13])=[CH:9][C:8]([O:15][CH3:16])=[C:7]([O:17][CH3:18])[CH:6]=2)=[O:31])[CH3:28]

Participants

6

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 178486677HCID 178486677, compound

Product 1

HCID 14626124HCID 14626124, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 3-hydroxy-6,7-dimethoxy-1-methyl-4-nitroisoquinoline (1.90 g, 7.19 mmol) in methylene chloride (100 mL) were added triethylamine (1.5 mL, 10.78 mmol), 4-dimethylaminopyridine (176 mg, 1.44 mmol) followed by diethylcarbamoyl chloride (0.81 mL, 8.62 mmol) in 5 mL of methylene chloride), added over a 10 minute period. The addition of each of the last three reagents was repeated twice two hours apart and then the mixture was stirred at room temperature overnight. The clear dark red-brown solution was washed with water (3×150 mL), saturated sodium bicarbonate solution and again with water. The organic phase was dried (Na2SO4), filtered and evaporated to dryness in vacuo. The tan residue was recrystallized from methylene chloride/ether to yield the title compound (2.04 g, 92.1%), mp 220°-221° C. (d). IR (KBr): 1738, 1520, 1260 cm-1. NMR (CDCl3): δ 1.24 and 1.28 [two t, J=7 Hz, total 6H, N(CH2CH3)2 ], 2.90 (s, 3H, 1-CH3), 3.20-3.80 (m, 4H, N(CH2CH3)2), 4.03 (s, 6H, 5,6-OCH3), 7.24 (s, 1H, 5- or 8-H), 7.28 (s, 1H, 5- or 8-H); MS (DCI): 364 (MH)+

Workup

  1. additionadded over a 10 minute period
  2. additionThe addition of each of the last three reagents
  3. washThe clear dark red-brown solution was washed with water (3×150 mL), saturated sodium bicarbonate solution and again with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customThe tan residue was recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-6f540dd768e944898a5e6d6eafadf57e
Source dataset
uspto-grants-1989_11
Patent number
US04880817

Reaction notes

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