Ammonium Bicarbonate → HCID 18786356, compound

HRID 1418465Notes

Reaction equation

HRID 1418465 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]([OH:28])=O)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(=O)(O)[O-].[NH4+].C(OC1C=CC2C(=CC=CC=2)[N:38]1C(OCC)=O)C>ClCCl>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]([NH2:38])=[O:28])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 14013Ammonium Bicarbonate2×HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline2×HCID 18786346HCID 18786346, compound

Product 1

HCID 18786356HCID 18786356, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-[3-[4-(pyrrol-1-ylmethyl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylic acid (0.36 g, 0.93 mmol), ammonium bicarbonate (0.44 g, 5.58 mmol) and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.28 g, 1.12 mmol) in dichloromethane (20 ml) were stirred at room temperature overnight. Ammonium bicarbonate and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline were added until the acid was consumed. The reaction mixture was diluted with dichloromethane (50 ml) and washed with water (50 ml). The organic extract was washed with cold 1N hydrochloric acid (50 ml), water (50 ml) and saturated aqueous sodium bicarbonate (5 ml), water (50 ml) and brine (50 ml), dried (magnesium sulfate) and concentrated to dryness. Recrystallization of the residue from ethyl acetate afforded the titled compound (198 mg, 54%).

Workup

  1. customwas consumed
  2. additionThe reaction mixture was diluted with dichloromethane (50 ml)
  3. washwashed with water (50 ml)
  4. extractionThe organic extract
  5. washwas washed with cold 1N hydrochloric acid (50 ml), water (50 ml) and saturated aqueous sodium bicarbonate (5 ml), water (50 ml) and brine (50 ml)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated to dryness
  8. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-7239ad586e2d4284bc2bd711c4a65ce9
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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