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2,6-Dichloro-3-methylaniline → 8-(cyclopentyloxy)-4-(2,6-dichloro-3-methylphenylamino)-7-methoxy-2H-chromen-2-one

HRID 20645
Notes
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Reaction equation

HRID 20645 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[C:17]2[C:12](=[C:13]([O:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[O:11][C:10](=[O:26])[CH:9]=1.[Cl:27][C:28]1[C:34]([CH3:35])=[CH:33][CH:32]=[C:31]([Cl:36])[C:29]=1[NH2:30].OP([O-])(O)=O.[K+]>CS(C)=O>[CH:21]1([O:20][C:13]2[C:14]([O:18][CH3:19])=[CH:15][CH:16]=[C:17]3[C:12]=2[O:11][C:10](=[O:26])[CH:9]=[C:8]3[NH:30][C:29]2[C:31]([Cl:36])=[CH:32][CH:33]=[C:34]([CH3:35])[C:28]=2[Cl:27])[CH2:25][CH2:24][CH2:23][CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1165292,6-Dichloro-3-methylanilineHCID 516951Monobasic potassium phosphateHCID 23665647Potassium tert-butoxideHCID 771747944-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248494778-(cyclopentyloxy)-4-(2,6-dichloro-3-methylphenylamino)-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium t-butoxide (35 mg, 0.3 mmol) was added to a solution of 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (29 mg, 0.1 mmol, Example 7, Step 1), 2,6-dichloro-3-methylaniline (26 mg, 0.15 mmol), and DMSO (1 mL). After 14 h, the reaction was poured into 1M KH2PO4 (20 mL), and extracted with ethyl acetate (20 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (4:1→0:1; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-4-(2,6-dichloro-3-methylphenylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.38 (s, 1H), 7.95 (d, 1H), 7.58 (d, 1H), 7.48 (d, 1H), 7.18 (d, 1H), 4.82 (m, 1H), 4.33 (s, 1H), 3.90 (s, 3H), 2.40 (s, 3H), 1.90-1.45 (m, 8H); MS (ESI): 433.9.

Workup

  1. extractionextracted with ethyl acetate (20 mL×2)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (4:1→0:1; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-25a63d98a37b4e3c9603f7eb11e4e24c
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745646B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes