Hydrochloric Acid → HCID 23365875, compound

HRID 1723241Notes

Reaction equation

HRID 1723241 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1[O:23][CH3:24])([O-:3])=[O:2].[H-].[Na+].[C:27](OC(=O)C)(=[O:29])[CH3:28].Cl>CN(C)C=O>[C:27]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=2[O:23][CH3:24])=[CH:8]1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 10269207HCID 10269207, compound

Product 1

HCID 23365875HCID 23365875, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-(5-nitroindol-3-ylmethyl)-3-methoxybenzoic acid (0.6 g.) in N,N-dimethylformamide (DMF), (3 ml.) was added to a stirred suspension of oil-free sodium hydride (0.088 g.) in DMF (8 ml.) under a nitrogen atmosphere at ambient temperature. The red solution was stirred for 20 minutes, and acetic anhydride (0.187 g.) added. After 1 hour, the mixture was poured into hydrochloric acid (1N, 30 ml.), extracted with ethyl acetate (3×50 ml), the combined extracts washed with water (2×20 ml.), brine, dried (MgSO4) and evaporated. The product was crystallized from a mixture of tetrahydrofuran and ether to give 4-(1-acetyl-5-nitroindol-3-ylmethyl)-3-methoxybenzoic acid (0.455 g., 67%) as a yellow powder; partial NMR (250 MHz, DMSO-d6): 2.68(s,3H, NCOCH3); 3.95(s,3H, OMe); 4.13(s,2H, ArCH3).

Workup

  1. waitAfter 1 hour
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washthe combined extracts washed with water (2×20 ml.), brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe product was crystallized from a mixture of tetrahydrofuran and ether

Sources & evidence

ORD record
ord-7317f75e1be340a69abd715d1e218ab8
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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