Methanol → HCID 12798059, compound

HRID 1659523Notes

Reaction equation

HRID 1659523 reaction equation
C[O:2][C:3]([CH:5]1[CH2:17][CH:16]2[CH2:18][CH2:19][CH:6]1[C:7]1[NH:8][C:9]3[C:14]([C:15]=12)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:4].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH:6]12[CH2:19][CH2:18][CH:16]([C:15]3[C:14]4[C:9]([NH:8][C:7]=31)=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:17][CH:5]2[C:3]([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 12798058HCID 12798058, compound

Product 1

HCID 12798059HCID 12798059, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 1,2,3,4-tetrahydro-1,4-ethanocarbazole-2-carboxylic acid methyl ester (13.0 g, 0.05 mole, described in Example 1), potassium carbonate (7.0 g, 0.05 mole), methanol (160 ml) and water (40 ml) was refluxed for 4 hr (oil bath at 90° C.) and stirred at room temperature for 18 hr. The reaction mixture was poured into water (500 ml) and washed with diethyl ether (2×). The aqueous phase was acidified with hydrochloric acid IN (100 ml) and extracted with diethyl ether (3×). Organic layers were washed with a saturated sodium chloride solution, dried and evaporated to dryness to afford the title compound (12 g). Crystallization afforded a total of 7.5 g of title compound: mp 212°-214° C.; NMR (DMSO-d6) δ 1.7 (m, 6H), 2.8 (m, 1H), 3.5 (m, 2H), 6.7-7.5 (m, 4H), 10.9 (s, 1H) and 11.8 (br, 1H); and Anal. Calcd for C15H15O2N: C, 74.66% H, 6.27% N, 5.81% and Found: C, 74.67% H, 6.48% N, 5.80%.

Workup

  1. washwashed with diethyl ether (2×)
  2. extractionextracted with diethyl ether (3×)
  3. washOrganic layers were washed with a saturated sodium chloride solution
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8a7a37a2fbec4cd085f07af9ad01e0a8
Source dataset
uspto-grants-1981_12
Patent number
US04304772

Reaction notes

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