Sodium Methoxide → 10-(3-Chlorophenyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indol-10-ol

HRID 1076711Notes

Reaction equation

HRID 1076711 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2([OH:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]2[NH:18][CH2:19][CH2:20][CH2:21]Cl)[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+]>CO>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2([OH:23])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]3[CH2:21][CH2:20][CH2:19][N:18]=[C:10]23)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178479601HCID 178479601, compound

Product 1

HCID 3782510-(3-Chlorophenyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indol-10-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(m-Chlorophenyl)-2-(3-chloropropylamino)-3H-indol-3-ol hydrochloride (0.742 g.) was dissolved in methanol (10 ml.) containing sodium methoxide (0.27 g.) and left at room temperature for 64 hours. The solution was evaporated to a foam which was triturated with water. The product was isolated as a white powder (546 mg.), m.p. 186°-187°C. Recrystallisation from acetonitrile raised the melting point to 190°-192°C.

Workup

  1. customThe solution was evaporated to a foam which
  2. customwas triturated with water
  3. customThe product was isolated as a white powder (546 mg.), m.p. 186°-187°C
  4. customRecrystallisation from acetonitrile
  5. temperatureraised the melting point to 190°-192°C.

Sources & evidence

ORD record
ord-84e5b253bdbc4c1c8d49e478bc6307d6
Source dataset
uspto-grants-1976_05
Patent number
US03957819

Reaction notes

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