Phosphorus oxychloride → 1,3a-Dimethyl-3,3a,5,6-tetrahydro-4-oxa-2,10b-diazafluoranthene

HRID 1660339Notes

Reaction equation

HRID 1660339 reaction equation
[CH3:1][C:2]1([CH2:15][NH:16][C:17](=O)[CH3:18])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.P(Cl)(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:18][C:17]1[N:8]2[C:7]3[C:2]([CH3:1])([O:3][CH2:4][CH2:5][C:6]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:15][N:16]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 127081801-(Acetamidomethyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

Product 1

HCID 127081821,3a-Dimethyl-3,3a,5,6-tetrahydro-4-oxa-2,10b-diazafluoranthene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-acetamide (2.7 g, described in Example 1), phosphorus oxychloride (1.8 ml) and dry benzene (150 ml) is stirred and refluxed for 2 hours, cooled and washed with water (10° C.). The aqueouslayer is separated, basified with 5N sodium hydroxide, and extracted with chloroform. The combined organic extracts are dried over magnesium sulfate, filtered and evaporated to give a residue of the title compound. The residue is dissolved in diethyl ether and hydrogen chloride is added until precipitation is completed. The precipitate is collected and crystallized from ethanol-diethyl ether to obtain the hydrochloride salt of the title compound (1.45 g); mp 226°-227° C.; ir(CHCl3) 2500, 1815, 1623, 1536, 1662 and 1575 cm-1 ; mr (CDCI3) δ 1.66 (s), 2.90 (m), 3.32 (s), 3,48 (d), 4.30 (m) and 7.51 (m).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled
  3. washwashed with water (10° C.)
  4. customThe aqueouslayer is separated
  5. extractionextracted with chloroform
  6. dry with materialThe combined organic extracts are dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-cd688fb59b8c47e1bffb2a1051d23590
Source dataset
uspto-grants-1981_12
Patent number
US04307234

Reaction notes

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