Ammonia → HCID 12800954, compound

HRID 225134Notes

Reaction equation

HRID 225134 reaction equation
[CH3:1][C:2]1([CH:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])[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.[NH3:21]>>[OH:17][CH2:18][CH2:19][CH:15]([C:2]1([CH3:1])[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)[C:16]([NH2:21])=[O:20]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 12507637HCID 12507637, compound

Product 1

HCID 12800954HCID 12800954, compound

Conditions

Temperature
90 °C

Procedure

A suspension of 4,5-dihydro-3-(1,3,4,9-tetrahydro-1-methyl pyrano[3,4-b]indol-1-yl)-2(3H)-furanone (described in Example 1, 20 g, 0.073 mole) in liquid ammonia is heated at 90° C. in a pressure apparatus for three hours. The apparatus is rinsed with ethanol and the yellow solution is evaporated. The residue is crystallized from methanol to afford α-(2-hydroxyethyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetamide (16.15 g), mp 159°-161° C.

Workup

  1. washThe apparatus is rinsed with ethanol
  2. customthe yellow solution is evaporated
  3. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-d79e3ac6429e4e7cbb32228580b8ce10
Source dataset
uspto-grants-1980_11
Patent number
US04235901

Reaction notes

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