Hydrochloric Acid → 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxy-N-(2-methylphenylsulfonyl)benzamide

HRID 1741922Notes

Reaction equation

HRID 1741922 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[CH:9]=[C:8]2[CH2:15][C:16]1[CH:34]=[CH:33][C:19]([C:20]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])(=[O:25])=[O:24])=[O:21])=[CH:18][C:17]=1[O:35][CH3:36])=[O:4].[OH-].[Na+].Cl>O1CCCC1>[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[CH:9]=[C:8]2[CH2:15][C:16]1[CH:34]=[CH:33][C:19]([C:20]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])(=[O:25])=[O:24])=[O:21])=[CH:18][C:17]=1[O:35][CH3:36])([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 151044784-(5-methoxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxy-N-(2-methylphenylsulfonyl)benzamide

Product 1

HCID 151044754-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxy-N-(2-methylphenylsulfonyl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(5-methoxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxy-N-(2-methylphenylsulfonyl)benzamide (130.0 g), tetrahydrofuran (1.0 L) and 1N sodium hydroxide (1.0 L) was heated to about 60° C. overnight, then treated with additional 1N sodium hydroxide (200 mL) and heated an additional 5 hours at 60° C. (likely unnecessary). The cooled reaction mixture was acidified with 6N hydrochloric acid (250 mL) and extracted with ethyl acetate. The ethyl acetate solution was washed with brine (three times), dried (MgSO4) and evaporated to give a solid which was dried at 50° C. under vacuum to give 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxy-N-(2-methylphenylsulfonyl)benzamide (12.9 g, 100% when calculated as 0.45 hydrate), mp 255°-257° C.; NMR (300 MHz, DMSO-d6): 2.60 (s, 3H, ArCH3), 3.76 (s, 3H, NCH3), 3.91 (s, 3H, OCH3), 4.05 (s, 2H, ArCH2Ar'), 7.15 (d, 1H), 7.19 (s, 1H), 7.39-7.51 (m, 5H), 7.58 (br t, 1H), 7.72 (dd, 1H), 8.03 (dd, 1H), 8.14 (d, 1H).

Workup

  1. temperatureheated an additional 5 hours at 60° C. (likely unnecessary)
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate solution was washed with brine (three times)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a solid which
  8. customwas dried at 50° C. under vacuum

Sources & evidence

ORD record
ord-88034314ad6d43ccad59bdcfcdcc0844
Source dataset
uspto-grants-1994_08
Patent number
US05334765

Reaction notes

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