Hydrochloric Acid → HCID 10294971, compound

HRID 899294Notes

Reaction equation

HRID 899294 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]([C:18]2[CH:27]=[C:26]3[C:21]([C:22]([CH3:30])([CH3:29])[CH2:23][CH2:24][N:25]3[CH3:28])=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH3:28][N:25]1[C:26]2[C:21](=[CH:20][CH:19]=[C:18]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=3)[CH:27]=2)[C:22]([CH3:29])([CH3:30])[CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69217139HCID 69217139, compound

Product 1

HCID 10294971HCID 10294971, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-[2-(1,4,4-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-heptyloxy]-benzoic acid methyl ester (1.1 g, 2.6 mmole) in 14 mL of a 1:1 THF/methanol mixture was treated with a solution of 0.44 g of lithium hydroxide monohydrate in 5 mL of water and stirred at 40° C. for 6 hours. The mixture was diluted with 20 mL of water and the pH was adjusted to 2.0 with 2N HCl solution. The mixture was extracted with three 20 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by preparative tlc (SiO2, 25% ethyl acetate in hexanes) to yield 0.875 g of 4-[2-(1,4,4-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-heptyloxy]-benzoic acid as a pale yellow oil. MS (EI): (M++1): 410.

Workup

  1. extractionThe mixture was extracted with three 20 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. customThe product was purified by preparative tlc (SiO2, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-00c5fdb6f18b410da3ee625a7e069048
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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