1,3-Dibromopropane → 10-Phenyl-2,3,4,10-tetrahydropyrimido[1,2-a]indol-10-ol

HRID 1579527Notes

Reaction equation

HRID 1579527 reaction equation
[NH2:1][C:2]1[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:19][CH2:20][CH2:21]Br>C(O)(C)C>[C:12]1([C:10]2([OH:11])[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]3[CH2:19][CH2:20][CH2:21][N:1]=[C:2]23)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 215687052-amino-3-phenyl-3H-indol-3-ol

Product 1

HCID 1507593810-Phenyl-2,3,4,10-tetrahydropyrimido[1,2-a]indol-10-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Amino-3-phenyl-3H-indol-3-ol (2.24 g) was heated under reflux with isopropanol (20 ml) and 1,3-dibromopropane (2.0 g) for 20 hours. The reaction mixture was evaporated to 10 ml and diluted with a little ether. The title compound was obtained as its hydrobromide salt 0.73 g., m.p. 260°-262°C (decomp.) and could be recrystallized from methanol, ethanol or isopropanol with or without the addition of ethyl acetate or ether.

Workup

  1. customThe reaction mixture was evaporated to 10 ml
  2. additiondiluted with a little ether

Sources & evidence

ORD record
ord-4d5a026f279c4f2688f8270abe7bd5c8
Source dataset
uspto-grants-1976_01
Patent number
US03931226

Reaction notes

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