1-Bromooctane → HCID 86646635, compound

HRID 525983Notes

Reaction equation

HRID 525983 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:7](=[C:8]([OH:17])[C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[C:16]2[C:7](=[C:8]([O:17][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 178488803HCID 178488803, compound

Product 1

HCID 86646635HCID 86646635, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-methoxyacridin-9-ol (2.0 g, 8.88 mmol), 1-bromooctane (2.17 g, 11.24 mmol), and potassium carbonate (7.91 g, 57.2 mmol) was mixed in N,N-dimethylformamide and heated at 120° C. for 8 h and the potassium carbonate was filtered off. The reaction mixture was quenched with water and extracted two times with ether and the combined organic phases was then washed once with 1M HCl, two times with water, and evaporated to obtain a yellow solid. The solid was recrystallised in methanol to give 4-methoxy-9-(octyloxy)acridine (0.95 g, 2.82 mmol) as yellow crystals. 1H-NMR (CDCl3, δ): 0.881 (t, 3H), 1.2-1.4 (m, 10H), 1.924 (m, 2H), 3.985 (s, 3H), 4.507 (t, 2H), 7.2-7.3 (m, 3H), 7.621 (d, 1H), 7.707 (m, 1H), 8.181 (m, 1H), 8.498 (m, 1H) MS MALDI-TOF (m/z): 337.146

Workup

  1. filtrationthe potassium carbonate was filtered off
  2. customThe reaction mixture was quenched with water
  3. extractionextracted two times with ether
  4. washthe combined organic phases was then washed once with 1M HCl, two times with water
  5. customevaporated
  6. customto obtain a yellow solid
  7. customThe solid was recrystallised in methanol

Sources & evidence

ORD record
ord-6ddc9e2a8a114d76aa39a73e0a007f58
Source dataset
uspto-grants-2016_05
Patent number
US09343198B2

Reaction notes

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