Sodium Hydroxide → HCID 69673439, compound

HRID 2276334Notes

Reaction equation

HRID 2276334 reaction equation
[CH3:1][C:2]1[C:11]([CH:12]([CH2:17][CH2:18][CH3:19])[C:13]([O:15]C)=[O:14])=[C:10]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:9]2[C:4](=[CH:5][C:6]3[CH2:29][CH2:28][CH2:27][C:7]=3[CH:8]=2)[N:3]=1.[OH-].[Na+]>CO.C(O)C>[CH3:1][C:2]1[C:11]([CH:12]([CH2:17][CH2:18][CH3:19])[C:13]([OH:15])=[O:14])=[C:10]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[C:9]2[C:8]3[CH2:29][CH2:28][CH2:27][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69673138HCID 69673138, compound

Product 1

HCID 69673439HCID 69673439, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-(2-methyl-4-p-tolyl-7,8-dihydro-6H-cyclopenta[g]quinolin-3-yl)pentanoate and methyl 2-(3-methyl-4-p-tolyl-8,9-dihydro-6H-cyclopenta[g]quinolin-3-yl)pentanoate (0.316 g; 0.81 mmol) in a mixture methanol-ethanol (2:1) (24 mL) was added a 5% sodium hydroxide solution (24.46 mmol; 19.5 mL) and the reaction mixture was heated to 60° C. for 18 h. The organic volatiles were removed under reduced pressure and the remaining basic solution was acidified to pH 2 with a 1N hydrochloric solution and the aqueous layer was extracted with ethyl acetate. The organics were combined, dried over magnesium sulfate and concentrated under reduced pressure. Purification by preparative HPLC (method 1) furnished 0.003 g (1%) of 2-(3-methyl-1-p-tolyl-8,9-dihydro-7H-cyclopenta[f]quinolin-2-yl)pentanoic acid. ESI/APCI(+): 374 (M+H). 1H NMR (CDCl3) δ 7.90 (d, J=8.35 Hz, 1H, H-9); 7.53 (d, J=8.35 Hz, 1H, H-8); 7.27 (bs, 1H, H-6′); 7.26 (bs, 1H, H-5′); 7.25 (d, J=8.2 Hz, 1H, H-3′); 7.06 (d, J=8.2 Hz, 1H, H-2′); 3.83 (t, J=6.7 Hz, 1H, H-12); 2.89, (m, 2H, H-7); 2.72 (s, 3H, H-10); 2.47 (s, 3H, H-7′); 2.22 (m, 1H, H-5); 2.18 (m, 1H, H-13); 2.02 (m, 1H, H-5); 1.84 (m, 1H, H-6); 1.76 (m, 1H, H-6); 1.63 (m, 1H, H-13); 1.19 (m, 1H, H-14); 0.97 (m, 1H, H-14); 0.737 (t, J=7.3 Hz, 3H, H-15). 13C NMR (CDCl3) δ 177.4 (C-11); 155.7 (C-2); 148.1 (C-4); 145.4 (C-9a); 143.1 (C-7a); 139.8 (C-4b); 137.9 (C-4′); 136.6 (C-1′); 131.5 (C-3); 129.8 (C-2′); 129.7 (C-3′); 128.9 (C-6′); 128.5 (C-5′); 126.7 (C-9); 126.6 (C-8); 124.1 (C-4a); 46.04 (C-12); 34.12 (C-5); 33.12 (C-7); 32.77 (C-13); 25.25 (C-6); 23.50 (C-10); 21.44 (C-14); 21.40 (C-7′); 14.14 (C-15).

Workup

  1. customThe organic volatiles were removed under reduced pressure
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by preparative HPLC (method 1)

Sources & evidence

ORD record
ord-6b1f20b39a9742a0a829201aeba02440
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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