Ethanol → HCID 136334098, compound

HRID 645470Notes

Reaction equation

HRID 645470 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[C:16]#[N:17])[CH:12]([NH:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=1)[CH2:11][CH2:10]2)=O.C([OH:34])C.OO.[OH-].[Na+]>O>[CH3:1][O:2][CH2:3][C:4]1[NH:17][C:16](=[O:34])[C:15]2[C:7](=[CH:8][C:9]3[CH2:10][CH2:11][CH:12]([NH:18][C:19]4[CH:20]=[CH:21][C:22]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])=[CH:30][CH:31]=4)[C:13]=3[CH:14]=2)[N:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 57435682HCID 57435682, compound

Product 1

HCID 136334098HCID 136334098, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl 4-[N-(5-methoxyacetamido-6-cyanoindan-1-yl)-amino]benzoate (0.295 g, 0.70 mmol), ethanol (3.2 ml), and water (0.64 ml) was cooled in an ice-bath, then 30% aqueous H2O2 solution (0.60 ml) was added followed by granulated sodium hydroxide pellets (0.047 g, 1.19 mmol). The reaction mixture was stirred at ˜0° C. for 10 mm, then it was placed in an oil bath preheated to 55° C. and stirred at this temperature for 30 min. The reaction mixture was allowed to cool to room temperature, then the solvents were removed in vacuo and the residue was suspended in water (˜15 ml). The pH of this mixture was adjusted to ˜12 with 1N NaOH (got a clear solution), then to ˜4 with 1N hydrochloric acid. The off white precipitate was collected by filtration, washed with water, dried in vacuo over P2O5: 0.262 g (89%), m.p. >122° C. (softens); 1H-NMR (250 MHz, DMSO-d6, TMS) 1.50 (s, 9H, C(CH3)3), 1.87, 2.56 (2×m, each 1H, 7-H), 3.00 (m, 2H, 8-H), 3.34 (s, 3H, OCH3), 4.30 (s, 2H, 2-CH2), 5.16 (m, 1H, 6-H), 6.78 (d, J=8.55 Hz, 2H, 3′, 5′-H), 6.89 (d, J=8.10, N10—H), 7.52, 7.90 (2×s, each 1H, 5-H, 9-H), 7.67 (d, J=8.45 Hz, 2′, 6′-H), 12.12 (s, 1H, N3—H); MS (ESI, m/z) 444 {(M+Na)+, 40%}; Found: C, 67.19, H, 6.31; N, 969. C24H27N3O40.5H2O requires C, 66.96; H, 6.50; N, 9.76%.

Workup

  1. temperaturewas cooled in an ice-bath
  2. customit was placed in an oil bath
  3. custompreheated to 55° C.
  4. stirringstirred at this temperature for 30 min
  5. temperatureto cool to room temperature
  6. customthe solvents were removed in vacuo
  7. filtrationThe off white precipitate was collected by filtration
  8. washwashed with water
  9. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-0530232e36ab40ea87cfad282910a4d4
Source dataset
uspto-grants-2010_04
Patent number
US07705006B2

Reaction notes

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