Methanol → HCID 9886905, compound

HRID 413802Notes

Reaction equation

HRID 413802 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:20]([O:22]C)=[O:21].CO.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18522125HCID 18522125, compound

Product 1

HCID 9886905HCID 9886905, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl N-(3,4-Dichlorobenzyl)-4-(3-hydroxypropyloxy)indole-2-carboxylate (6.9 g) was dissolved in THF (140 ml) and methanol (140 ml) and sodium hydroxide (3M, 110 ml) was added and the reaction stirred for 16 hours. The reaction was then concentrated in vacuo and the residue dissolved in water. The solution was acidified by dropwise addition of acetic acid, resulting in the precipitation of a white solid which was filtered, washed with water and dried in vacuo to give the desired end product (5.58 g. 84%); NMR d (CD3SOCD3) 1.92 (m, 2H), 3.60 (dd, 2H), 4.13 (dd, 2H), 5.89 (s, 2H), 6.52 (s, 1H), 6.94-7.11 (m, 4H), 7.32 (d, 1H), 7.47 (d, 1H); M/z (−) 392 (M−H+).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. dissolutionthe residue dissolved in water
  3. additionThe solution was acidified by dropwise addition of acetic acid
  4. customresulting in the precipitation of a white solid which
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried in vacuo
  8. customto give the desired end product (5.58 g. 84%)

Sources & evidence

ORD record
ord-17d085106c3e4095bf828ec7e119e11b
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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