Acetic Anhydride → HCID 131715564, compound

HRID 1253311Notes

Reaction equation

HRID 1253311 reaction equation
[ClH:1].[OH:2][C@H:3]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:8][C:7]2[C:18]([N+:22]([O-:24])=[O:23])=[CH:19][CH:20]=[CH:21][C:6]=2[N:5]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:4]1=[O:30].[C:31](OC(=O)C)(=[O:33])[CH3:32]>>[ClH:1].[C:31]([O:2][C@H:3]1[C@@H:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:8][C:7]2[C:18]([N+:22]([O-:24])=[O:23])=[CH:19][CH:20]=[CH:21][C:6]=2[N:5]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:4]1=[O:30])(=[O:33])[CH3:32]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 131715565HCID 131715565, compound

Product 1

HCID 131715564HCID 131715564, compound

Conditions

Temperature
100 °C

Procedure

A stirred suspension of the hydrochloride salt of (cis)-3-(hydroxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-nitro-2H-1-benzazepin-2-one, monohydrochloride (approximately 1.93 mmol) in 30 ml of acetic anhydride was heated to 100° C. (oil bath) and the resulting solution heated at 110°-120° C. for 4.5 hours. After removing the bulk of acetic anhydride on a rotary evaporator at 0.2 mm, the solid residue (2 g) was rubbed under 10 ml of ethyl acetate and diluted portionwise with 20 ml of ether. After cooling overnight, the colorless solid was filtered under argon, washed with ether and dried in vacuo; yield, 0.84 g; melting point 198°-200° C. (dec.), s. 192° C.

Workup

  1. temperaturethe resulting solution heated at 110°-120° C. for 4.5 hours
  2. customAfter removing the bulk of acetic anhydride
  3. customon a rotary evaporator at 0.2 mm
  4. additiondiluted portionwise with 20 ml of ether
  5. temperatureAfter cooling overnight
  6. filtrationthe colorless solid was filtered under argon
  7. washwashed with ether
  8. customdried in vacuo
  9. customyield
  10. custom192° C.

Sources & evidence

ORD record
ord-2d834a0933de4c57ac93dc1cd548d1d3
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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