O-Phenylenediamine → HCID 23072367, compound

HRID 1182478Notes

Reaction equation

HRID 1182478 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:10].[C:21]1([NH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH2:27].C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[NH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:28][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:10]

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58982104HCID 58982104, compound

Product 1

HCID 23072367HCID 23072367, compoundYield 3.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromo-7-[(2-naphthoyl)]heptane 72 (62 mg, 0.17 mmol) in toluene (2 mL) and DMF (1 mL) was added 1,2-phenylenediamine (60 mg, 0.56 mmol) and N,N-diisopropylethylamine (36 μL, 0.21 mmol) and the reaction mixture was stirred at room temperature for 2 hours then at 75° C. for two hours and finally refluxed for 5 hours. Saturated sodium bicarbonate solution (5 mL) was added and the mixture was extracted with dichloromethane (2×20 mL). The combined organic layers were washed with deionized water (20 mL), washed with brine (10 mL), and dried (MgSO4). The solvents were removed in vacuo and the title compound 73 (2 mg, 3%) was isolated by column chromatography (3:7-4:6 ethyl acetate:hexane) followed by recrystallization from ether and hexane. 1H NMR (400 MHz, DMSO-d6): δ 8.69 (s, 1H), 8.14 (d, J=8.0 Hz, 1H), 8.00 (m, 3H), 7.64 (m, 2H), 6.52 (m, 1H), 6.47 (m, 1H), 6.38 (m, 2H), 4.46 (s, 2H), 4.30 (m, 1H), 3.17 (t, J=7.4 Hz, 2H), 2.99 (m, 2H), 1.69 (m, 2H), 1.60 (m, 2H), 1.39 (m, 6H).

Workup

  1. waitat 75° C. for two hours
  2. temperaturefinally refluxed for 5 hours
  3. extractionthe mixture was extracted with dichloromethane (2×20 mL)
  4. washThe combined organic layers were washed with deionized water (20 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-48074dace6d8406aaf8383d644aeaf78
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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